NPASS Compound

Structure

NPC18128 OpenBabel07101718292D 23 24 0 0 0 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 19 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 15 2 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	328.267
LogP:	2.932
LogD:	2.966
LogS:	-3.624
# Rotatable Bonds:	6
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.714
Synthetic Accessibility Score:	2.43
Fsp3:	0.222
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:	-4.996
MDCK Permeability:	1.4071957593841944e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.115
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	94.42892456054688%
Volume Distribution (VD):	0.44
Pgp-substrate:	1.3855876922607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.114
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.225
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.671
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	11.196
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.703
Skin Sensitization:	0.94
Carcinogencity:	0.026
Eye Corrosion:	0.012
Eye Irritation:	0.928
Respiratory Toxicity:	0.255

Download Data

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

Natural Product: NPC18128

Natural Product ID:	NPC18128
*Common Name:**	Gramistilbenoid C
IUPAC Name:	5-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-2-(2-hydroxyethyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	ASTBSZWPSFQWBN-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C18H20O5/c1-22-14-7-12(8-15(11-14)23-2)3-4-13-9-17(20)16(5-6-19)18(21)10-13/h3-4,7-11,19-21H,5-6H2,1-2H3/b4-3+
SMILES:	COc1cc(/C=C/c2cc(c(CCO)c(c2)O)O)cc(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431357
PubChem CID:	72702681
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
NPO6006	Arundina graminifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24063582]
NPO6006	Arundina graminifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
ORGANISM	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5900.0	nM	PMID[458194]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	8700.0	nM	PMID[458194]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5500.0	nM	PMID[458194]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	=	4800.0	nM	PMID[458194]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6200.0	nM	PMID[458194]
NPT2	Others	Unspecified		Activity	=	99.0	%	PMID[458195]
NPT23310	ORGANISM	Norovirus	Norovirus	Activity	=	200.8	%	PMID[458195]

☑ 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 NPC18128 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	345
0.1-0.2	1554
0.2-0.3	4594
0.3-0.4	12936
0.4-0.5	5256
0.5-0.6	4553
0.6-0.7	8259
0.7-0.8	4127
0.8-0.85	723
0.85-0.9	305
0.9-0.95	41
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC77789
0.9652	High Similarity	NPC184302
0.9565	High Similarity	NPC190514
0.9478	High Similarity	NPC69261
0.9478	High Similarity	NPC33270
0.9391	High Similarity	NPC150624
0.931	High Similarity	NPC127894
0.931	High Similarity	NPC219070
0.931	High Similarity	NPC15860
0.931	High Similarity	NPC470759
0.9304	High Similarity	NPC53906
0.9304	High Similarity	NPC808
0.9262	High Similarity	NPC473221
0.9256	High Similarity	NPC476254
0.9256	High Similarity	NPC131397
0.925	High Similarity	NPC474160
0.9244	High Similarity	NPC476633
0.9224	High Similarity	NPC114064
0.9217	High Similarity	NPC276737
0.9217	High Similarity	NPC22610
0.918	High Similarity	NPC82299
0.9145	High Similarity	NPC474933
0.9145	High Similarity	NPC244816
0.9145	High Similarity	NPC50521
0.9145	High Similarity	NPC221549
0.913	High Similarity	NPC261343
0.912	High Similarity	NPC472590
0.9106	High Similarity	NPC236760
0.9098	High Similarity	NPC105031
0.9083	High Similarity	NPC212965
0.906	High Similarity	NPC85292
0.906	High Similarity	NPC229147
0.906	High Similarity	NPC203113
0.906	High Similarity	NPC141090
0.906	High Similarity	NPC54507
0.9008	High Similarity	NPC120638
0.9	High Similarity	NPC102639
0.9	High Similarity	NPC218753
0.8974	High Similarity	NPC167934
0.8974	High Similarity	NPC185541
0.8974	High Similarity	NPC464
0.8974	High Similarity	NPC232165
0.896	High Similarity	NPC472797
0.8952	High Similarity	NPC242032
0.8943	High Similarity	NPC105925
0.8943	High Similarity	NPC113495
0.8934	High Similarity	NPC261992
0.8926	High Similarity	NPC75713
0.8915	High Similarity	NPC476698
0.8908	High Similarity	NPC131118
0.8889	High Similarity	NPC180508
0.8889	High Similarity	NPC228287
0.888	High Similarity	NPC274717
0.888	High Similarity	NPC38604
0.888	High Similarity	NPC211179
0.888	High Similarity	NPC266691
0.8871	High Similarity	NPC283049
0.8871	High Similarity	NPC26879
0.8871	High Similarity	NPC50315
0.8871	High Similarity	NPC170485
0.8871	High Similarity	NPC230479
0.887	High Similarity	NPC168657
0.887	High Similarity	NPC94045
0.887	High Similarity	NPC2682
0.8862	High Similarity	NPC270030
0.8852	High Similarity	NPC188997
0.8846	High Similarity	NPC134260
0.8833	High Similarity	NPC137294
0.8833	High Similarity	NPC85895
0.8833	High Similarity	NPC121866
0.8828	High Similarity	NPC269528
0.8824	High Similarity	NPC195466
0.8819	High Similarity	NPC471517
0.881	High Similarity	NPC472796
0.881	High Similarity	NPC469951
0.881	High Similarity	NPC476968
0.881	High Similarity	NPC170844
0.881	High Similarity	NPC472795
0.881	High Similarity	NPC212015
0.881	High Similarity	NPC469963
0.88	High Similarity	NPC159968
0.88	High Similarity	NPC169474
0.88	High Similarity	NPC246620
0.88	High Similarity	NPC124452
0.88	High Similarity	NPC236791
0.88	High Similarity	NPC82679
0.88	High Similarity	NPC293054
0.88	High Similarity	NPC46978
0.88	High Similarity	NPC324112
0.88	High Similarity	NPC282000
0.88	High Similarity	NPC74817
0.879	High Similarity	NPC278955
0.879	High Similarity	NPC105718
0.8783	High Similarity	NPC33728
0.8783	High Similarity	NPC19808
0.878	High Similarity	NPC282496
0.878	High Similarity	NPC76465
0.878	High Similarity	NPC95168
0.878	High Similarity	NPC233526
0.878	High Similarity	NPC38761
0.878	High Similarity	NPC121115
0.878	High Similarity	NPC136319
0.875	High Similarity	NPC218884
0.875	High Similarity	NPC48781
0.875	High Similarity	NPC9592
0.874	High Similarity	NPC51840
0.874	High Similarity	NPC299221
0.874	High Similarity	NPC224157
0.874	High Similarity	NPC234488
0.874	High Similarity	NPC311680
0.874	High Similarity	NPC192687
0.873	High Similarity	NPC470213
0.873	High Similarity	NPC53986
0.873	High Similarity	NPC98631
0.873	High Similarity	NPC38017
0.873	High Similarity	NPC215300
0.873	High Similarity	NPC206615
0.873	High Similarity	NPC186843
0.873	High Similarity	NPC38664
0.872	High Similarity	NPC214406
0.872	High Similarity	NPC78974
0.872	High Similarity	NPC18924
0.872	High Similarity	NPC28730
0.872	High Similarity	NPC276212
0.872	High Similarity	NPC44748
0.872	High Similarity	NPC103823
0.872	High Similarity	NPC223136
0.872	High Similarity	NPC223953
0.8718	High Similarity	NPC280606
0.871	High Similarity	NPC138248
0.871	High Similarity	NPC228503
0.8699	High Similarity	NPC36016
0.8699	High Similarity	NPC100099
0.8696	High Similarity	NPC245115
0.8696	High Similarity	NPC174981
0.8692	High Similarity	NPC256262
0.8692	High Similarity	NPC255147
0.8692	High Similarity	NPC61946
0.8692	High Similarity	NPC201357
0.8692	High Similarity	NPC261873
0.8692	High Similarity	NPC283009
0.8692	High Similarity	NPC111655
0.8692	High Similarity	NPC281521
0.8682	High Similarity	NPC11060
0.8682	High Similarity	NPC475840
0.8682	High Similarity	NPC469610
0.8672	High Similarity	NPC282508
0.8672	High Similarity	NPC474017
0.8672	High Similarity	NPC103799
0.8672	High Similarity	NPC8899
0.8661	High Similarity	NPC190144
0.8661	High Similarity	NPC10225
0.8661	High Similarity	NPC471519
0.8661	High Similarity	NPC222108
0.8661	High Similarity	NPC93962
0.8661	High Similarity	NPC16577
0.8661	High Similarity	NPC134360
0.8661	High Similarity	NPC96719
0.8661	High Similarity	NPC58164
0.8661	High Similarity	NPC471518
0.8651	High Similarity	NPC66331
0.8651	High Similarity	NPC53781
0.8647	High Similarity	NPC210192
0.864	High Similarity	NPC293801
0.864	High Similarity	NPC117214
0.864	High Similarity	NPC60885
0.864	High Similarity	NPC298757
0.864	High Similarity	NPC17809
0.864	High Similarity	NPC221077
0.864	High Similarity	NPC116907
0.864	High Similarity	NPC57490
0.864	High Similarity	NPC251855
0.864	High Similarity	NPC17943
0.864	High Similarity	NPC265483
0.864	High Similarity	NPC103420
0.864	High Similarity	NPC208950
0.864	High Similarity	NPC299584
0.864	High Similarity	NPC475169
0.864	High Similarity	NPC233410
0.864	High Similarity	NPC33654
0.864	High Similarity	NPC82483
0.864	High Similarity	NPC472093
0.864	High Similarity	NPC285040
0.864	High Similarity	NPC203133
0.864	High Similarity	NPC188022
0.864	High Similarity	NPC234400
0.864	High Similarity	NPC102540
0.864	High Similarity	NPC193544
0.8636	High Similarity	NPC184613
0.8632	High Similarity	NPC224527
0.8632	High Similarity	NPC296920
0.8632	High Similarity	NPC90520
0.8629	High Similarity	NPC96940
0.8626	High Similarity	NPC472649
0.8626	High Similarity	NPC141717
0.8626	High Similarity	NPC16435
0.8626	High Similarity	NPC472800
0.8626	High Similarity	NPC306441
0.8626	High Similarity	NPC170328
0.8626	High Similarity	NPC472336

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 NPC18128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	937
0.2-0.3	1635
0.3-0.4	2735
0.4-0.5	1726
0.5-0.6	1053
0.6-0.7	635
0.7-0.8	117
0.8-0.85	3
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD3027	Phase 3
0.872	High Similarity	NPD6917	Clinical (unspecified phase)
0.8661	High Similarity	NPD4625	Phase 3
0.8629	High Similarity	NPD4749	Approved
0.8594	High Similarity	NPD6410	Clinical (unspecified phase)
0.8583	High Similarity	NPD4908	Phase 1
0.8468	Intermediate Similarity	NPD1610	Phase 2
0.8462	Intermediate Similarity	NPD1613	Approved
0.8462	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD1548	Phase 1
0.8305	Intermediate Similarity	NPD4750	Phase 3
0.8295	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2861	Phase 2
0.8049	Intermediate Similarity	NPD6671	Approved
0.7939	Intermediate Similarity	NPD3018	Phase 2
0.7907	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD6100	Approved
0.7883	Intermediate Similarity	NPD6099	Approved
0.7863	Intermediate Similarity	NPD846	Approved
0.7863	Intermediate Similarity	NPD940	Approved
0.7842	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1607	Approved
0.7786	Intermediate Similarity	NPD3892	Phase 2
0.7778	Intermediate Similarity	NPD2238	Phase 2
0.7778	Intermediate Similarity	NPD1242	Phase 1
0.7769	Intermediate Similarity	NPD2983	Phase 2
0.7769	Intermediate Similarity	NPD2982	Phase 2
0.7752	Intermediate Similarity	NPD422	Phase 1
0.7752	Intermediate Similarity	NPD1091	Approved
0.775	Intermediate Similarity	NPD968	Approved
0.7739	Intermediate Similarity	NPD844	Approved
0.771	Intermediate Similarity	NPD6696	Suspended
0.7692	Intermediate Similarity	NPD2981	Phase 2
0.7681	Intermediate Similarity	NPD1510	Phase 2
0.766	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1240	Approved
0.7626	Intermediate Similarity	NPD1551	Phase 2
0.76	Intermediate Similarity	NPD5283	Phase 1
0.7597	Intermediate Similarity	NPD4626	Approved
0.7597	Intermediate Similarity	NPD1778	Approved
0.7569	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7447	Phase 1
0.7557	Intermediate Similarity	NPD2233	Approved
0.7557	Intermediate Similarity	NPD2230	Approved
0.7557	Intermediate Similarity	NPD2232	Approved
0.7541	Intermediate Similarity	NPD290	Approved
0.7538	Intermediate Similarity	NPD3496	Discontinued
0.7521	Intermediate Similarity	NPD288	Approved
0.752	Intermediate Similarity	NPD7635	Approved
0.7518	Intermediate Similarity	NPD4060	Phase 1
0.7517	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7213	Phase 3
0.75	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.748	Intermediate Similarity	NPD2684	Approved
0.7464	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5124	Phase 1
0.7463	Intermediate Similarity	NPD6584	Phase 3
0.745	Intermediate Similarity	NPD37	Approved
0.745	Intermediate Similarity	NPD1934	Approved
0.7447	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD228	Approved
0.7436	Intermediate Similarity	NPD2859	Approved
0.7436	Intermediate Similarity	NPD2860	Approved
0.7432	Intermediate Similarity	NPD4380	Phase 2
0.7429	Intermediate Similarity	NPD7033	Discontinued
0.7424	Intermediate Similarity	NPD2235	Phase 2
0.7424	Intermediate Similarity	NPD2231	Phase 2
0.7413	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4097	Suspended
0.7395	Intermediate Similarity	NPD3020	Approved
0.7394	Intermediate Similarity	NPD1549	Phase 2
0.7386	Intermediate Similarity	NPD6746	Phase 2
0.7385	Intermediate Similarity	NPD5691	Approved
0.7381	Intermediate Similarity	NPD7843	Approved
0.7353	Intermediate Similarity	NPD600	Approved
0.7353	Intermediate Similarity	NPD596	Approved
0.735	Intermediate Similarity	NPD2933	Approved
0.735	Intermediate Similarity	NPD2934	Approved
0.7348	Intermediate Similarity	NPD1611	Approved
0.7344	Intermediate Similarity	NPD709	Approved
0.7344	Intermediate Similarity	NPD7157	Approved
0.7343	Intermediate Similarity	NPD5177	Phase 3
0.7333	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD2532	Approved
0.7329	Intermediate Similarity	NPD2534	Approved
0.7324	Intermediate Similarity	NPD5763	Approved
0.7324	Intermediate Similarity	NPD5762	Approved
0.7324	Intermediate Similarity	NPD3540	Phase 1
0.7323	Intermediate Similarity	NPD1398	Phase 1
0.7319	Intermediate Similarity	NPD839	Approved
0.7319	Intermediate Similarity	NPD840	Approved
0.7313	Intermediate Similarity	NPD8651	Approved
0.7303	Intermediate Similarity	NPD4966	Approved
0.7303	Intermediate Similarity	NPD4967	Phase 2
0.7303	Intermediate Similarity	NPD4965	Approved
0.7293	Intermediate Similarity	NPD1608	Approved
0.7292	Intermediate Similarity	NPD3750	Approved
0.729	Intermediate Similarity	NPD6232	Discontinued
0.7287	Intermediate Similarity	NPD7340	Approved
0.7285	Intermediate Similarity	NPD2801	Approved
0.728	Intermediate Similarity	NPD3022	Approved
0.728	Intermediate Similarity	NPD3021	Approved
0.728	Intermediate Similarity	NPD5451	Approved
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1511	Approved
0.7259	Intermediate Similarity	NPD2797	Approved
0.7258	Intermediate Similarity	NPD2342	Discontinued
0.7255	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3539	Phase 1
0.7254	Intermediate Similarity	NPD2796	Approved
0.7252	Intermediate Similarity	NPD1651	Approved
0.7241	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6582	Phase 2
0.7239	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6583	Phase 3
0.7234	Intermediate Similarity	NPD4536	Approved
0.7234	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD6959	Discontinued
0.7222	Intermediate Similarity	NPD1652	Phase 2
0.7209	Intermediate Similarity	NPD2557	Approved
0.7208	Intermediate Similarity	NPD6234	Discontinued
0.7197	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6166	Phase 2
0.719	Intermediate Similarity	NPD3882	Suspended
0.719	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1283	Approved
0.7185	Intermediate Similarity	NPD3225	Approved
0.7181	Intermediate Similarity	NPD1653	Approved
0.7172	Intermediate Similarity	NPD4628	Phase 3
0.7171	Intermediate Similarity	NPD7819	Suspended
0.717	Intermediate Similarity	NPD5844	Phase 1
0.7163	Intermediate Similarity	NPD2568	Approved
0.7162	Intermediate Similarity	NPD1512	Approved
0.7152	Intermediate Similarity	NPD7473	Discontinued
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6559	Discontinued
0.7133	Intermediate Similarity	NPD4005	Discontinued
0.7133	Intermediate Similarity	NPD6032	Approved
0.7132	Intermediate Similarity	NPD3094	Phase 2
0.7124	Intermediate Similarity	NPD5402	Approved
0.7124	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2677	Approved
0.7122	Intermediate Similarity	NPD3268	Approved
0.7121	Intermediate Similarity	NPD3444	Approved
0.7121	Intermediate Similarity	NPD3445	Approved
0.7121	Intermediate Similarity	NPD3443	Approved
0.7121	Intermediate Similarity	NPD5585	Approved
0.7109	Intermediate Similarity	NPD5535	Approved
0.7103	Intermediate Similarity	NPD6674	Discontinued
0.7103	Intermediate Similarity	NPD3060	Approved
0.7095	Intermediate Similarity	NPD3157	Approved
0.7095	Intermediate Similarity	NPD3158	Phase 1
0.7095	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5735	Approved
0.709	Intermediate Similarity	NPD3705	Approved
0.7086	Intermediate Similarity	NPD4675	Approved
0.7086	Intermediate Similarity	NPD4678	Approved
0.7086	Intermediate Similarity	NPD6599	Discontinued
0.7083	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD6004	Phase 3
0.7083	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6002	Phase 3
0.708	Intermediate Similarity	NPD3691	Phase 2
0.708	Intermediate Similarity	NPD4624	Approved
0.708	Intermediate Similarity	NPD3690	Phase 2
0.7078	Intermediate Similarity	NPD7768	Phase 2
0.7077	Intermediate Similarity	NPD6387	Discontinued
0.7068	Intermediate Similarity	NPD2668	Approved
0.7068	Intermediate Similarity	NPD5126	Approved
0.7068	Intermediate Similarity	NPD2667	Approved
0.7068	Intermediate Similarity	NPD5846	Approved
0.7068	Intermediate Similarity	NPD5125	Phase 3
0.7068	Intermediate Similarity	NPD17	Approved
0.7068	Intermediate Similarity	NPD6516	Phase 2
0.7063	Intermediate Similarity	NPD5960	Phase 3
0.7063	Intermediate Similarity	NPD5588	Approved
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7055	Intermediate Similarity	NPD7466	Approved
0.7047	Intermediate Similarity	NPD6090	Discontinued
0.7045	Intermediate Similarity	NPD3091	Approved
0.7039	Intermediate Similarity	NPD7411	Suspended
0.7032	Intermediate Similarity	NPD7075	Discontinued
0.7027	Intermediate Similarity	NPD6799	Approved
0.7027	Intermediate Similarity	NPD7041	Phase 2
0.7027	Intermediate Similarity	NPD4357	Discontinued
0.7027	Intermediate Similarity	NPD7040	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