NPASS Compound

Structure

CID75713 OpenBabel06191715412D 21 22 0 0 0 0 0 0 0 0999 V2000 -6.0622 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -2.5981 2.5000 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 2.5000 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 0.0000 1.0000 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 -4.3301 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 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	302.181
LogP:	3.223
LogD:	3.593
LogS:	-4.22
# Rotatable Bonds:	5
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.853
Synthetic Accessibility Score:	2.095
Fsp3:	0.176
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:	-4.863
MDCK Permeability:	1.3352268069866113e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.766
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	96.4619369506836%
Volume Distribution (VD):	0.679
Pgp-substrate:	2.7095494270324707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.679
CYP2C9-inhibitor:	0.391
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.609
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.405

ADMET: Excretion

Clearance (CL):	11.102
Half-life (T1/2):	0.75

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.507
AMES Toxicity:	0.366
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.356
Skin Sensitization:	0.932
Carcinogencity:	0.184
Eye Corrosion:	0.037
Eye Irritation:	0.923
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC75713

Natural Product ID:	NPC75713
*Common Name:**	Phoyunbene D
IUPAC Name:	3-[(E)-2-(2,3-dimethoxyphenyl)ethenyl]-5-methoxyphenol
Synonyms:	Phoyunbene D
Standard InCHIKey:	JTNSCGPJCOQOIF-BQYQJAHWSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-19-15-10-12(9-14(18)11-15)7-8-13-5-4-6-16(20-2)17(13)21-3/h4-11,18H,1-3H3/b8-7+
SMILES:	COc1cc(/C=C/c2cccc(c2OC)OC)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2012419
PubChem CID:	11601663
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[560227]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[560227]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	80500.0	nM	PMID[560227]

☑ 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 NPC75713 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	362
0.1-0.2	1876
0.2-0.3	6068
0.3-0.4	13402
0.4-0.5	3532
0.5-0.6	4503
0.6-0.7	7823
0.7-0.8	3970
0.8-0.85	658
0.85-0.9	376
0.9-0.95	112
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC95168
0.9661	High Similarity	NPC265483
0.9661	High Similarity	NPC82483
0.9661	High Similarity	NPC105925
0.9661	High Similarity	NPC299584
0.958	High Similarity	NPC18924
0.958	High Similarity	NPC78974
0.958	High Similarity	NPC214406
0.958	High Similarity	NPC44748
0.958	High Similarity	NPC103823
0.958	High Similarity	NPC28730
0.958	High Similarity	NPC223136
0.9569	High Similarity	NPC166759
0.95	High Similarity	NPC159968
0.95	High Similarity	NPC293054
0.95	High Similarity	NPC282000
0.95	High Similarity	NPC324112
0.95	High Similarity	NPC74817
0.95	High Similarity	NPC246620
0.95	High Similarity	NPC236760
0.95	High Similarity	NPC169474
0.95	High Similarity	NPC124452
0.95	High Similarity	NPC236791
0.95	High Similarity	NPC82679
0.9496	High Similarity	NPC234400
0.9496	High Similarity	NPC60885
0.9492	High Similarity	NPC233526
0.9492	High Similarity	NPC121115
0.9492	High Similarity	NPC282496
0.9483	High Similarity	NPC474565
0.9421	High Similarity	NPC266691
0.9417	High Similarity	NPC223953
0.9407	High Similarity	NPC262253
0.9407	High Similarity	NPC473411
0.9407	High Similarity	NPC71579
0.9344	High Similarity	NPC10225
0.9344	High Similarity	NPC58164
0.9333	High Similarity	NPC203133
0.9333	High Similarity	NPC221077
0.9333	High Similarity	NPC193544
0.9333	High Similarity	NPC116907
0.9333	High Similarity	NPC17943
0.9333	High Similarity	NPC298757
0.9333	High Similarity	NPC251855
0.9333	High Similarity	NPC233410
0.9333	High Similarity	NPC472093
0.9333	High Similarity	NPC117214
0.9333	High Similarity	NPC208950
0.9333	High Similarity	NPC475169
0.9333	High Similarity	NPC57490
0.9268	High Similarity	NPC311680
0.9268	High Similarity	NPC126836
0.9268	High Similarity	NPC224157
0.9268	High Similarity	NPC299221
0.9268	High Similarity	NPC234488
0.9268	High Similarity	NPC51840
0.9268	High Similarity	NPC192687
0.9262	High Similarity	NPC28765
0.9262	High Similarity	NPC154866
0.9224	High Similarity	NPC33270
0.9224	High Similarity	NPC69261
0.9187	High Similarity	NPC469951
0.9187	High Similarity	NPC212015
0.9187	High Similarity	NPC469963
0.9187	High Similarity	NPC190144
0.918	High Similarity	NPC216836
0.918	High Similarity	NPC242032
0.918	High Similarity	NPC252131
0.918	High Similarity	NPC127587
0.918	High Similarity	NPC210355
0.918	High Similarity	NPC266555
0.9167	High Similarity	NPC228922
0.9167	High Similarity	NPC136319
0.9167	High Similarity	NPC197757
0.9153	High Similarity	NPC10932
0.9153	High Similarity	NPC61516
0.9153	High Similarity	NPC247364
0.9153	High Similarity	NPC232084
0.9138	High Similarity	NPC203113
0.9138	High Similarity	NPC150624
0.9138	High Similarity	NPC123948
0.912	High Similarity	NPC6451
0.9113	High Similarity	NPC214860
0.9113	High Similarity	NPC229231
0.9106	High Similarity	NPC186843
0.9106	High Similarity	NPC470213
0.9106	High Similarity	NPC206615
0.9106	High Similarity	NPC98631
0.9098	High Similarity	NPC112596
0.9098	High Similarity	NPC76451
0.9091	High Similarity	NPC183446
0.9083	High Similarity	NPC41562
0.9068	High Similarity	NPC184302
0.9068	High Similarity	NPC475961
0.9068	High Similarity	NPC254625
0.9068	High Similarity	NPC226629
0.906	High Similarity	NPC219070
0.906	High Similarity	NPC470759
0.906	High Similarity	NPC127894
0.906	High Similarity	NPC15860
0.9052	High Similarity	NPC53906
0.9052	High Similarity	NPC808
0.9048	High Similarity	NPC37196
0.9048	High Similarity	NPC94236
0.9048	High Similarity	NPC168059
0.9048	High Similarity	NPC36661
0.9048	High Similarity	NPC269528
0.9048	High Similarity	NPC475840
0.9048	High Similarity	NPC471390
0.9048	High Similarity	NPC471391
0.9048	High Similarity	NPC32778
0.9048	High Similarity	NPC229442
0.904	High Similarity	NPC232275
0.904	High Similarity	NPC474356
0.904	High Similarity	NPC45715
0.904	High Similarity	NPC12275
0.9032	High Similarity	NPC45824
0.9032	High Similarity	NPC170844
0.9032	High Similarity	NPC476968
0.9	High Similarity	NPC476633
0.9	High Similarity	NPC285289
0.8983	High Similarity	NPC190514
0.8976	High Similarity	NPC317380
0.8974	High Similarity	NPC114064
0.8968	High Similarity	NPC127624
0.8968	High Similarity	NPC86655
0.8968	High Similarity	NPC161203
0.8968	High Similarity	NPC202762
0.8966	High Similarity	NPC276737
0.8966	High Similarity	NPC180508
0.8966	High Similarity	NPC228287
0.8966	High Similarity	NPC22610
0.896	High Similarity	NPC63574
0.896	High Similarity	NPC472338
0.896	High Similarity	NPC184814
0.896	High Similarity	NPC91291
0.8952	High Similarity	NPC63179
0.8947	High Similarity	NPC94045
0.8934	High Similarity	NPC228972
0.8934	High Similarity	NPC122792
0.8934	High Similarity	NPC5796
0.8934	High Similarity	NPC206487
0.8926	High Similarity	NPC135414
0.8926	High Similarity	NPC18128
0.8926	High Similarity	NPC270326
0.8926	High Similarity	NPC246967
0.8926	High Similarity	NPC474864
0.8926	High Similarity	NPC77789
0.8917	High Similarity	NPC102639
0.8917	High Similarity	NPC472596
0.8908	High Similarity	NPC20674
0.8906	High Similarity	NPC283009
0.8906	High Similarity	NPC112246
0.8906	High Similarity	NPC256262
0.8906	High Similarity	NPC112939
0.8906	High Similarity	NPC470356
0.8906	High Similarity	NPC313081
0.8906	High Similarity	NPC474206
0.8906	High Similarity	NPC61946
0.8906	High Similarity	NPC255147
0.8906	High Similarity	NPC281521
0.8906	High Similarity	NPC158142
0.8906	High Similarity	NPC195022
0.8906	High Similarity	NPC69029
0.8906	High Similarity	NPC472337
0.8906	High Similarity	NPC94750
0.8906	High Similarity	NPC108198
0.8906	High Similarity	NPC121812
0.8906	High Similarity	NPC261873
0.8906	High Similarity	NPC134968
0.8906	High Similarity	NPC201357
0.8906	High Similarity	NPC294884
0.8906	High Similarity	NPC200557
0.8906	High Similarity	NPC10314
0.8906	High Similarity	NPC111655
0.8898	High Similarity	NPC474933
0.8898	High Similarity	NPC50521
0.8898	High Similarity	NPC244816
0.8898	High Similarity	NPC259638
0.8898	High Similarity	NPC221549
0.8889	High Similarity	NPC470095
0.8889	High Similarity	NPC470096
0.8889	High Similarity	NPC464
0.8889	High Similarity	NPC185541
0.8889	High Similarity	NPC15543
0.8889	High Similarity	NPC474017
0.8889	High Similarity	NPC472597
0.888	High Similarity	NPC226788
0.888	High Similarity	NPC285339
0.888	High Similarity	NPC210623
0.888	High Similarity	NPC3439
0.888	High Similarity	NPC228769
0.888	High Similarity	NPC222004
0.888	High Similarity	NPC218856
0.888	High Similarity	NPC202582
0.888	High Similarity	NPC273295
0.888	High Similarity	NPC190629
0.888	High Similarity	NPC470258
0.888	High Similarity	NPC470633
0.8871	High Similarity	NPC474119

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 NPC75713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	1003
0.2-0.3	1815
0.3-0.4	2762
0.4-0.5	1584
0.5-0.6	961
0.6-0.7	580
0.7-0.8	106
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD3027	Phase 3
0.8871	High Similarity	NPD3018	Phase 2
0.8699	High Similarity	NPD2983	Phase 2
0.8699	High Similarity	NPD2982	Phase 2
0.8651	High Similarity	NPD1529	Clinical (unspecified phase)
0.8618	High Similarity	NPD2981	Phase 2
0.8571	High Similarity	NPD1530	Clinical (unspecified phase)
0.8527	High Similarity	NPD1613	Approved
0.8527	High Similarity	NPD1612	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5283	Phase 1
0.8235	Intermediate Similarity	NPD228	Approved
0.8217	Intermediate Similarity	NPD4908	Phase 1
0.8211	Intermediate Similarity	NPD1548	Phase 1
0.8154	Intermediate Similarity	NPD4625	Phase 3
0.8148	Intermediate Similarity	NPD3540	Phase 1
0.811	Intermediate Similarity	NPD4749	Approved
0.811	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1610	Phase 2
0.8092	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD3539	Phase 1
0.7923	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD1242	Phase 1
0.784	Intermediate Similarity	NPD5536	Phase 2
0.782	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD2801	Approved
0.7801	Intermediate Similarity	NPD4357	Discontinued
0.7769	Intermediate Similarity	NPD2922	Phase 1
0.7769	Intermediate Similarity	NPD4750	Phase 3
0.774	Intermediate Similarity	NPD1934	Approved
0.7703	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6671	Approved
0.7674	Intermediate Similarity	NPD1091	Approved
0.7674	Intermediate Similarity	NPD422	Phase 1
0.7627	Intermediate Similarity	NPD846	Approved
0.7627	Intermediate Similarity	NPD940	Approved
0.7623	Intermediate Similarity	NPD3022	Approved
0.7623	Intermediate Similarity	NPD3021	Approved
0.7603	Intermediate Similarity	NPD4678	Approved
0.7603	Intermediate Similarity	NPD4675	Approved
0.7603	Intermediate Similarity	NPD290	Approved
0.7594	Intermediate Similarity	NPD2861	Phase 2
0.7586	Intermediate Similarity	NPD1653	Approved
0.7578	Intermediate Similarity	NPD1357	Approved
0.7574	Intermediate Similarity	NPD1558	Phase 1
0.7568	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1511	Approved
0.7538	Intermediate Similarity	NPD3705	Approved
0.7535	Intermediate Similarity	NPD2219	Phase 1
0.7535	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD968	Approved
0.7518	Intermediate Similarity	NPD5177	Phase 3
0.7518	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.7483	Intermediate Similarity	NPD7124	Phase 2
0.7451	Intermediate Similarity	NPD6232	Discontinued
0.7448	Intermediate Similarity	NPD1512	Approved
0.7445	Intermediate Similarity	NPD1240	Approved
0.7445	Intermediate Similarity	NPD4060	Phase 1
0.7429	Intermediate Similarity	NPD6099	Approved
0.7429	Intermediate Similarity	NPD6100	Approved
0.7417	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4005	Discontinued
0.7414	Intermediate Similarity	NPD9296	Approved
0.74	Intermediate Similarity	NPD3817	Phase 2
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7357	Intermediate Similarity	NPD1510	Phase 2
0.7355	Intermediate Similarity	NPD6166	Phase 2
0.7355	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4966	Approved
0.7351	Intermediate Similarity	NPD4967	Phase 2
0.7351	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4965	Approved
0.7343	Intermediate Similarity	NPD3892	Phase 2
0.7338	Intermediate Similarity	NPD1607	Approved
0.7329	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3620	Phase 2
0.731	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD1551	Phase 2
0.7303	Intermediate Similarity	NPD4055	Discovery
0.7286	Intermediate Similarity	NPD6111	Discontinued
0.7279	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4237	Approved
0.7273	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD4236	Phase 3
0.7266	Intermediate Similarity	NPD709	Approved
0.7266	Intermediate Similarity	NPD447	Suspended
0.7265	Intermediate Similarity	NPD2934	Approved
0.7265	Intermediate Similarity	NPD2933	Approved
0.726	Intermediate Similarity	NPD4123	Phase 3
0.726	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7447	Phase 1
0.7258	Intermediate Similarity	NPD2684	Approved
0.7252	Intermediate Similarity	NPD1778	Approved
0.7246	Intermediate Similarity	NPD2674	Phase 3
0.7239	Intermediate Similarity	NPD3225	Approved
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2230	Approved
0.7218	Intermediate Similarity	NPD2232	Approved
0.7218	Intermediate Similarity	NPD2233	Approved
0.7215	Intermediate Similarity	NPD7054	Approved
0.7203	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2859	Approved
0.7203	Intermediate Similarity	NPD2860	Approved
0.7203	Intermediate Similarity	NPD844	Approved
0.7197	Intermediate Similarity	NPD3496	Discontinued
0.7194	Intermediate Similarity	NPD2238	Phase 2
0.7192	Intermediate Similarity	NPD7213	Phase 3
0.7192	Intermediate Similarity	NPD7212	Phase 2
0.719	Intermediate Similarity	NPD291	Approved
0.7183	Intermediate Similarity	NPD2935	Discontinued
0.7179	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3145	Approved
0.7174	Intermediate Similarity	NPD3144	Approved
0.7174	Intermediate Similarity	NPD5111	Phase 2
0.7174	Intermediate Similarity	NPD5109	Approved
0.7174	Intermediate Similarity	NPD5110	Phase 2
0.717	Intermediate Similarity	NPD7074	Phase 3
0.717	Intermediate Similarity	NPD7472	Approved
0.7167	Intermediate Similarity	NPD3020	Approved
0.7165	Intermediate Similarity	NPD7843	Approved
0.7153	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD1424	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7133	Intermediate Similarity	NPD7266	Discontinued
0.7133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4380	Phase 2
0.7132	Intermediate Similarity	NPD7157	Approved
0.7132	Intermediate Similarity	NPD6584	Phase 3
0.7121	Intermediate Similarity	NPD4626	Approved
0.7111	Intermediate Similarity	NPD8651	Approved
0.7111	Intermediate Similarity	NPD6696	Suspended
0.7107	Intermediate Similarity	NPD5844	Phase 1
0.7103	Intermediate Similarity	NPD3750	Approved
0.7103	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1608	Approved
0.7086	Intermediate Similarity	NPD5090	Approved
0.7086	Intermediate Similarity	NPD5089	Approved
0.7083	Intermediate Similarity	NPD1549	Phase 2
0.708	Intermediate Similarity	NPD9494	Approved
0.7075	Intermediate Similarity	NPD5297	Approved
0.7075	Intermediate Similarity	NPD6799	Approved
0.7071	Intermediate Similarity	NPD943	Approved
0.7067	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5451	Approved
0.7059	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2797	Approved
0.7055	Intermediate Similarity	NPD2677	Approved
0.705	Intermediate Similarity	NPD5718	Phase 2
0.7044	Intermediate Similarity	NPD7228	Approved
0.7037	Intermediate Similarity	NPD7808	Phase 3
0.7034	Intermediate Similarity	NPD6674	Discontinued
0.7034	Intermediate Similarity	NPD1652	Phase 2
0.7023	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5124	Phase 1
0.7021	Intermediate Similarity	NPD1933	Approved
0.7021	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6797	Phase 2
0.7014	Intermediate Similarity	NPD5762	Approved
0.7014	Intermediate Similarity	NPD5763	Approved
0.7014	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6788	Approved
0.7	Intermediate Similarity	NPD288	Approved
0.6993	Remote Similarity	NPD1465	Phase 2
0.6993	Remote Similarity	NPD7033	Discontinued
0.6993	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5494	Approved
0.698	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7095	Approved
0.6975	Remote Similarity	NPD7251	Discontinued
0.6972	Remote Similarity	NPD4097	Suspended
0.697	Remote Similarity	NPD7533	Approved
0.697	Remote Similarity	NPD7534	Approved
0.6968	Remote Similarity	NPD7075	Discontinued
0.6967	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2235	Phase 2
0.6963	Remote Similarity	NPD2231	Phase 2
0.6959	Remote Similarity	NPD1774	Approved
0.6954	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8054	Approved
0.6951	Remote Similarity	NPD8053	Approved
0.6948	Remote Similarity	NPD5402	Approved
0.6944	Remote Similarity	NPD6032	Approved
0.6944	Remote Similarity	NPD2796	Approved
0.694	Remote Similarity	NPD3847	Discontinued
0.6939	Remote Similarity	NPD6190	Approved
0.6939	Remote Similarity	NPD5241	Discontinued
0.6934	Remote Similarity	NPD1203	Approved
0.6933	Remote Similarity	NPD5403	Approved
0.6933	Remote Similarity	NPD7549	Discontinued
0.6933	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6798	Discontinued

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