NPASS Compound

Structure

CID299584 OpenBabel06191716102D 22 23 0 0 0 0 0 0 0 0999 V2000 -6.9282 0.0000 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 0.8660 1.5000 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 -1.7321 -0.0000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 0.8660 -0.5000 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 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 12 17 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	310.971
LogP:	2.983
LogD:	3.231
LogS:	-4.279
# Rotatable Bonds:	5
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.829
Synthetic Accessibility Score:	2.324
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.798
MDCK Permeability:	1.2846072422689758e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	94.84590911865234%
Volume Distribution (VD):	0.495
Pgp-substrate:	3.603830575942993%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.672
CYP2C19-substrate:	0.434
CYP2C9-inhibitor:	0.344
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.532
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	10.728
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.337
AMES Toxicity:	0.172
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.27
Skin Sensitization:	0.933
Carcinogencity:	0.103
Eye Corrosion:	0.016
Eye Irritation:	0.937
Respiratory Toxicity:	0.452

Download Data

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

Natural Product: NPC299584

Natural Product ID:	NPC299584
*Common Name:**	Phoyunbene A
IUPAC Name:	3-[(E)-2-(3-hydroxy-5-methoxyphenyl)ethenyl]-2,6-dimethoxyphenol
Synonyms:	Phoyunbene A
Standard InCHIKey:	DYWOJJOORBDHBP-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C17H18O5/c1-20-14-9-11(8-13(18)10-14)4-5-12-6-7-15(21-2)16(19)17(12)22-3/h4-10,18-19H,1-3H3/b5-4+
SMILES:	COc1cc(/C=C/c2ccc(c(c2OC)O)OC)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2012416
PubChem CID:	11522311
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
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394543]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21656	Pholidota yunnanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21656	Pholidota yunnanensis	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	3

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[507077]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[507077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[507077]

☑ 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 NPC299584 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	388
0.1-0.2	1930
0.2-0.3	6463
0.3-0.4	12992
0.4-0.5	3553
0.5-0.6	4183
0.6-0.7	7205
0.7-0.8	4505
0.8-0.85	767
0.85-0.9	468
0.9-0.95	186
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265483
1.0	High Similarity	NPC82483
0.9916	High Similarity	NPC44748
0.9916	High Similarity	NPC28730
0.9916	High Similarity	NPC78974
0.9916	High Similarity	NPC214406
0.9916	High Similarity	NPC223136
0.9916	High Similarity	NPC18924
0.9916	High Similarity	NPC103823
0.9833	High Similarity	NPC169474
0.9833	High Similarity	NPC159968
0.9833	High Similarity	NPC74817
0.9833	High Similarity	NPC124452
0.9833	High Similarity	NPC236791
0.9833	High Similarity	NPC293054
0.9833	High Similarity	NPC282000
0.9833	High Similarity	NPC82679
0.9833	High Similarity	NPC246620
0.9833	High Similarity	NPC324112
0.9832	High Similarity	NPC234400
0.9832	High Similarity	NPC60885
0.9831	High Similarity	NPC95168
0.9746	High Similarity	NPC71579
0.9746	High Similarity	NPC262253
0.9746	High Similarity	NPC473411
0.9672	High Similarity	NPC58164
0.9672	High Similarity	NPC10225
0.9667	High Similarity	NPC221077
0.9667	High Similarity	NPC251855
0.9667	High Similarity	NPC57490
0.9667	High Similarity	NPC208950
0.9667	High Similarity	NPC233410
0.9667	High Similarity	NPC116907
0.9667	High Similarity	NPC117214
0.9667	High Similarity	NPC203133
0.9667	High Similarity	NPC193544
0.9667	High Similarity	NPC475169
0.9667	High Similarity	NPC298757
0.9667	High Similarity	NPC472093
0.9667	High Similarity	NPC105925
0.9667	High Similarity	NPC17943
0.9661	High Similarity	NPC75713
0.9593	High Similarity	NPC234488
0.9593	High Similarity	NPC299221
0.9593	High Similarity	NPC311680
0.9593	High Similarity	NPC126836
0.9593	High Similarity	NPC51840
0.959	High Similarity	NPC154866
0.959	High Similarity	NPC28765
0.9576	High Similarity	NPC166759
0.9512	High Similarity	NPC212015
0.9508	High Similarity	NPC252131
0.9508	High Similarity	NPC266555
0.9508	High Similarity	NPC210355
0.9508	High Similarity	NPC236760
0.9508	High Similarity	NPC127587
0.95	High Similarity	NPC282496
0.95	High Similarity	NPC197757
0.95	High Similarity	NPC136319
0.95	High Similarity	NPC121115
0.95	High Similarity	NPC228922
0.95	High Similarity	NPC233526
0.9492	High Similarity	NPC247364
0.9492	High Similarity	NPC474565
0.9492	High Similarity	NPC232084
0.9492	High Similarity	NPC61516
0.9492	High Similarity	NPC10932
0.944	High Similarity	NPC6451
0.9435	High Similarity	NPC214860
0.9431	High Similarity	NPC98631
0.9431	High Similarity	NPC206615
0.9431	High Similarity	NPC186843
0.9431	High Similarity	NPC266691
0.9431	High Similarity	NPC470213
0.9426	High Similarity	NPC223953
0.9426	High Similarity	NPC76451
0.9421	High Similarity	NPC183446
0.9417	High Similarity	NPC41562
0.9407	High Similarity	NPC226629
0.9365	High Similarity	NPC471391
0.9365	High Similarity	NPC475840
0.9365	High Similarity	NPC471390
0.9365	High Similarity	NPC229442
0.9365	High Similarity	NPC168059
0.9365	High Similarity	NPC32778
0.9365	High Similarity	NPC36661
0.936	High Similarity	NPC12275
0.936	High Similarity	NPC232275
0.936	High Similarity	NPC474356
0.936	High Similarity	NPC45715
0.9355	High Similarity	NPC476968
0.9355	High Similarity	NPC45824
0.9355	High Similarity	NPC170844
0.9291	High Similarity	NPC317380
0.9286	High Similarity	NPC86655
0.9286	High Similarity	NPC202762
0.9286	High Similarity	NPC127624
0.928	High Similarity	NPC91291
0.928	High Similarity	NPC192687
0.928	High Similarity	NPC224157
0.928	High Similarity	NPC472338
0.9262	High Similarity	NPC228972
0.9262	High Similarity	NPC122792
0.9262	High Similarity	NPC5796
0.9262	High Similarity	NPC206487
0.9244	High Similarity	NPC20674
0.9237	High Similarity	NPC259638
0.9219	High Similarity	NPC108198
0.9219	High Similarity	NPC474206
0.9219	High Similarity	NPC158142
0.9219	High Similarity	NPC472337
0.9219	High Similarity	NPC94750
0.9219	High Similarity	NPC69029
0.9219	High Similarity	NPC200557
0.9219	High Similarity	NPC121812
0.9219	High Similarity	NPC313081
0.9219	High Similarity	NPC112246
0.9219	High Similarity	NPC10314
0.9219	High Similarity	NPC256262
0.9219	High Similarity	NPC294884
0.9219	High Similarity	NPC112939
0.9219	High Similarity	NPC470356
0.9206	High Similarity	NPC472597
0.9206	High Similarity	NPC474017
0.9206	High Similarity	NPC470096
0.9206	High Similarity	NPC15543
0.9206	High Similarity	NPC470095
0.92	High Similarity	NPC470633
0.92	High Similarity	NPC469963
0.92	High Similarity	NPC228769
0.92	High Similarity	NPC190144
0.92	High Similarity	NPC469951
0.9194	High Similarity	NPC216836
0.9194	High Similarity	NPC242032
0.9194	High Similarity	NPC470699
0.918	High Similarity	NPC84086
0.9174	High Similarity	NPC145780
0.9174	High Similarity	NPC49341
0.9167	High Similarity	NPC229401
0.9153	High Similarity	NPC203113
0.9153	High Similarity	NPC123948
0.9153	High Similarity	NPC193067
0.9147	High Similarity	NPC143139
0.9147	High Similarity	NPC202846
0.9147	High Similarity	NPC16435
0.9147	High Similarity	NPC248727
0.9147	High Similarity	NPC265433
0.9147	High Similarity	NPC270456
0.9147	High Similarity	NPC227503
0.9147	High Similarity	NPC230734
0.9147	High Similarity	NPC474639
0.9147	High Similarity	NPC306441
0.9147	High Similarity	NPC472334
0.9147	High Similarity	NPC162659
0.9147	High Similarity	NPC472336
0.9141	High Similarity	NPC289258
0.9141	High Similarity	NPC276026
0.9141	High Similarity	NPC206737
0.9141	High Similarity	NPC56764
0.9141	High Similarity	NPC209199
0.9141	High Similarity	NPC125649
0.9141	High Similarity	NPC469659
0.9141	High Similarity	NPC555
0.9141	High Similarity	NPC7515
0.9141	High Similarity	NPC188378
0.9134	High Similarity	NPC160991
0.9134	High Similarity	NPC16208
0.9134	High Similarity	NPC184447
0.9134	High Similarity	NPC7903
0.9134	High Similarity	NPC201587
0.9134	High Similarity	NPC35932
0.9134	High Similarity	NPC253105
0.9127	High Similarity	NPC474481
0.9113	High Similarity	NPC181361
0.9113	High Similarity	NPC112596
0.9083	High Similarity	NPC475961
0.9083	High Similarity	NPC254625
0.9077	High Similarity	NPC6262
0.9077	High Similarity	NPC107551
0.9077	High Similarity	NPC276490
0.9077	High Similarity	NPC211549
0.9077	High Similarity	NPC474282
0.9077	High Similarity	NPC326797
0.9077	High Similarity	NPC102904
0.9077	High Similarity	NPC90615
0.9077	High Similarity	NPC176051
0.9077	High Similarity	NPC73535
0.9077	High Similarity	NPC103976
0.9077	High Similarity	NPC272157
0.9077	High Similarity	NPC56329
0.9077	High Similarity	NPC242715
0.9077	High Similarity	NPC201145
0.9077	High Similarity	NPC25111
0.907	High Similarity	NPC180602
0.907	High Similarity	NPC241241
0.907	High Similarity	NPC214853
0.907	High Similarity	NPC234333
0.907	High Similarity	NPC61946
0.907	High Similarity	NPC55239
0.907	High Similarity	NPC47398

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 NPC299584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	972
0.2-0.3	1963
0.3-0.4	2739
0.4-0.5	1548
0.5-0.6	857
0.6-0.7	589
0.7-0.8	111
0.8-0.85	10
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD3027	Phase 3
0.8968	High Similarity	NPD1529	Clinical (unspecified phase)
0.8889	High Similarity	NPD1530	Clinical (unspecified phase)
0.8889	High Similarity	NPD3018	Phase 2
0.8837	High Similarity	NPD1613	Approved
0.8837	High Similarity	NPD1612	Clinical (unspecified phase)
0.872	High Similarity	NPD2983	Phase 2
0.872	High Similarity	NPD2982	Phase 2
0.864	High Similarity	NPD2981	Phase 2
0.8571	High Similarity	NPD228	Approved
0.8425	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8279	Intermediate Similarity	NPD5283	Phase 1
0.8244	Intermediate Similarity	NPD4908	Phase 1
0.824	Intermediate Similarity	NPD1548	Phase 1
0.8175	Intermediate Similarity	NPD3540	Phase 1
0.8125	Intermediate Similarity	NPD1610	Phase 2
0.812	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD3539	Phase 1
0.8082	Intermediate Similarity	NPD2801	Approved
0.8014	Intermediate Similarity	NPD1934	Approved
0.7973	Intermediate Similarity	NPD3882	Suspended
0.7951	Intermediate Similarity	NPD3021	Approved
0.7951	Intermediate Similarity	NPD3022	Approved
0.791	Intermediate Similarity	NPD4625	Phase 3
0.7881	Intermediate Similarity	NPD1242	Phase 1
0.7874	Intermediate Similarity	NPD5536	Phase 2
0.7868	Intermediate Similarity	NPD1558	Phase 1
0.7863	Intermediate Similarity	NPD4749	Approved
0.7862	Intermediate Similarity	NPD1653	Approved
0.7838	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD4357	Discontinued
0.7832	Intermediate Similarity	NPD1511	Approved
0.7727	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1512	Approved
0.7721	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD422	Phase 1
0.7687	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD846	Approved
0.7667	Intermediate Similarity	NPD940	Approved
0.7635	Intermediate Similarity	NPD4678	Approved
0.7635	Intermediate Similarity	NPD4675	Approved
0.7632	Intermediate Similarity	NPD6234	Discontinued
0.763	Intermediate Similarity	NPD2861	Phase 2
0.7616	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1357	Approved
0.7613	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6166	Phase 2
0.7613	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3620	Phase 2
0.7609	Intermediate Similarity	NPD4060	Phase 1
0.7609	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3705	Approved
0.7576	Intermediate Similarity	NPD1091	Approved
0.7569	Intermediate Similarity	NPD2219	Phase 1
0.7569	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3060	Approved
0.755	Intermediate Similarity	NPD3817	Phase 2
0.7537	Intermediate Similarity	NPD2922	Phase 1
0.7536	Intermediate Similarity	NPD2674	Phase 3
0.7533	Intermediate Similarity	NPD37	Approved
0.752	Intermediate Similarity	NPD4750	Phase 3
0.7517	Intermediate Similarity	NPD7124	Phase 2
0.75	Intermediate Similarity	NPD290	Approved
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7482	Intermediate Similarity	NPD1240	Approved
0.7468	Intermediate Similarity	NPD7054	Approved
0.7464	Intermediate Similarity	NPD3144	Approved
0.7464	Intermediate Similarity	NPD3145	Approved
0.7458	Intermediate Similarity	NPD9296	Approved
0.7451	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4005	Discontinued
0.7442	Intermediate Similarity	NPD6671	Approved
0.744	Intermediate Similarity	NPD2684	Approved
0.7429	Intermediate Similarity	NPD230	Phase 1
0.7421	Intermediate Similarity	NPD7074	Phase 3
0.7421	Intermediate Similarity	NPD7472	Approved
0.7419	Intermediate Similarity	NPD7199	Phase 2
0.7413	Intermediate Similarity	NPD7266	Discontinued
0.7405	Intermediate Similarity	NPD3818	Discontinued
0.7394	Intermediate Similarity	NPD1510	Phase 2
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7376	Intermediate Similarity	NPD1607	Approved
0.7372	Intermediate Similarity	NPD9494	Approved
0.7365	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD943	Approved
0.7347	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7843	Approved
0.7342	Intermediate Similarity	NPD7473	Discontinued
0.7338	Intermediate Similarity	NPD4055	Discovery
0.7325	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6111	Discontinued
0.7315	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2934	Approved
0.7311	Intermediate Similarity	NPD2933	Approved
0.731	Intermediate Similarity	NPD4236	Phase 3
0.731	Intermediate Similarity	NPD5177	Phase 3
0.731	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4237	Approved
0.7308	Intermediate Similarity	NPD7157	Approved
0.7297	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4123	Phase 3
0.7297	Intermediate Similarity	NPD7447	Phase 1
0.7296	Intermediate Similarity	NPD7228	Approved
0.7292	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4380	Phase 2
0.728	Intermediate Similarity	NPD968	Approved
0.7279	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD6797	Phase 2
0.7255	Intermediate Similarity	NPD1465	Phase 2
0.725	Intermediate Similarity	NPD2859	Approved
0.725	Intermediate Similarity	NPD2860	Approved
0.7241	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7213	Phase 3
0.723	Intermediate Similarity	NPD7212	Phase 2
0.723	Intermediate Similarity	NPD6799	Approved
0.7222	Intermediate Similarity	NPD2935	Discontinued
0.7222	Intermediate Similarity	NPD6100	Approved
0.7222	Intermediate Similarity	NPD7251	Discontinued
0.7222	Intermediate Similarity	NPD6099	Approved
0.7214	Intermediate Similarity	NPD5109	Approved
0.7214	Intermediate Similarity	NPD5110	Phase 2
0.7214	Intermediate Similarity	NPD5111	Phase 2
0.7213	Intermediate Similarity	NPD3020	Approved
0.7211	Intermediate Similarity	NPD6190	Approved
0.7195	Intermediate Similarity	NPD8053	Approved
0.7195	Intermediate Similarity	NPD8054	Approved
0.7194	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1652	Phase 2
0.7192	Intermediate Similarity	NPD6674	Discontinued
0.7181	Intermediate Similarity	NPD1424	Approved
0.7178	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7808	Phase 3
0.7174	Intermediate Similarity	NPD6584	Phase 3
0.7172	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD2978	Approved
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7143	Intermediate Similarity	NPD2977	Approved
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7124	Intermediate Similarity	NPD5090	Approved
0.7124	Intermediate Similarity	NPD5089	Approved
0.7123	Intermediate Similarity	NPD1549	Phase 2
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7114	Intermediate Similarity	NPD5297	Approved
0.7113	Intermediate Similarity	NPD2238	Phase 2
0.7109	Intermediate Similarity	NPD5451	Approved
0.7105	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1551	Phase 2
0.7097	Intermediate Similarity	NPD291	Approved
0.7097	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2677	Approved
0.7092	Intermediate Similarity	NPD6798	Discontinued
0.7092	Intermediate Similarity	NPD5718	Phase 2
0.7083	Intermediate Similarity	NPD4536	Approved
0.7083	Intermediate Similarity	NPD4538	Approved
0.7083	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4162	Approved
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD447	Suspended
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6788	Approved
0.7045	Intermediate Similarity	NPD709	Approved
0.7037	Intermediate Similarity	NPD6516	Phase 2
0.7037	Intermediate Similarity	NPD5846	Approved
0.7037	Intermediate Similarity	NPD1778	Approved
0.7034	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3225	Approved
0.7027	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5494	Approved
0.702	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4097	Suspended
0.7007	Intermediate Similarity	NPD2233	Approved
0.7007	Intermediate Similarity	NPD2230	Approved
0.7007	Intermediate Similarity	NPD2232	Approved
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2796	Approved
0.6985	Remote Similarity	NPD3496	Discontinued
0.6985	Remote Similarity	NPD3847	Discontinued
0.698	Remote Similarity	NPD5241	Discontinued
0.697	Remote Similarity	NPD7549	Discontinued
0.6967	Remote Similarity	NPD844	Approved
0.6966	Remote Similarity	NPD6896	Approved
0.6966	Remote Similarity	NPD6895	Approved
0.6957	Remote Similarity	NPD6583	Phase 3
0.6957	Remote Similarity	NPD6582	Phase 2
0.6954	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1358	Approved
0.6949	Remote Similarity	NPD9094	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