NPASS Compound

Structure

NPC311530 OpenBabel07101718332D 28 30 0 0 1 0 0 0 0 0999 V2000 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 21 1 0 0 0 0 11 9 1 6 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 19 2 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 10 1 6 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.15
Volume:	383.31
LogP:	1.842
LogD:	2.343
LogS:	-3.751
# Rotatable Bonds:	7
TPSA:	95.84
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	3.373
Fsp3:	0.4
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:	-4.942
MDCK Permeability:	3.025829755642917e-05
Pgp-inhibitor:	0.722
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.275
Plasma Protein Binding (PPB):	62.360877990722656%
Volume Distribution (VD):	0.57
Pgp-substrate:	38.96391296386719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.924
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.783
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.454
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	8.984
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.776
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.868
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.166

Download Data

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

Natural Product: NPC311530

Natural Product ID:	NPC311530
*Common Name:**	4,6-Dimethoxy-5-Hydroxy-3-Hydroxymethyl-2-(3,4,5-Trimethoxyphenyl)-2,3-Dihydrobenzofuran
IUPAC Name:	(2S,3S)-3-(hydroxymethyl)-4,6-dimethoxy-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-5-ol
Synonyms:
Standard InCHIKey:	INACKEYIIKMUED-ADLMAVQZSA-N
Standard InCHI:	InChI=1S/C20H24O8/c1-23-13-8-12-16(20(27-5)17(13)22)11(9-21)18(28-12)10-6-14(24-2)19(26-4)15(7-10)25-3/h6-8,11,18,21-22H,9H2,1-5H3/t11-,18-/m1/s1
SMILES:	OC[C@H]1[C@H](Oc2c1c(OC)c(c(c2)OC)O)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224791
PubChem CID:	16216402
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792422]
NPO14922	Tarenna attenuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17343407]
NPO14922	Tarenna attenuata	Species	Rubiaceae	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	1
Others	4

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	58.0	%	PMID[482977]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	58.2	%	PMID[482977]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	55.0	%	PMID[482977]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	61.4	%	PMID[482977]
NPT1	Others	Radical scavenging activity		IC50	=	45000.0	nM	PMID[482977]

☑ 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 NPC311530 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	433
0.1-0.2	1467
0.2-0.3	4411
0.3-0.4	11368
0.4-0.5	7118
0.5-0.6	4151
0.6-0.7	6550
0.7-0.8	5341
0.8-0.85	939
0.85-0.9	681
0.9-0.95	226
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9776	High Similarity	NPC254759
0.9776	High Similarity	NPC160283
0.9706	High Similarity	NPC477616
0.9704	High Similarity	NPC247291
0.9701	High Similarity	NPC292882
0.9632	High Similarity	NPC107161
0.9562	High Similarity	NPC47633
0.9562	High Similarity	NPC85264
0.9562	High Similarity	NPC102044
0.9559	High Similarity	NPC263261
0.9559	High Similarity	NPC471389
0.9559	High Similarity	NPC87725
0.9552	High Similarity	NPC472336
0.9552	High Similarity	NPC472334
0.9549	High Similarity	NPC326095
0.9549	High Similarity	NPC244983
0.9493	High Similarity	NPC280092
0.9493	High Similarity	NPC12641
0.9493	High Similarity	NPC93323
0.9493	High Similarity	NPC45257
0.9493	High Similarity	NPC63879
0.9485	High Similarity	NPC184797
0.9485	High Similarity	NPC27495
0.9485	High Similarity	NPC309124
0.9478	High Similarity	NPC472337
0.9478	High Similarity	NPC134968
0.9429	High Similarity	NPC101376
0.9412	High Similarity	NPC319647
0.9412	High Similarity	NPC245207
0.9412	High Similarity	NPC473739
0.9412	High Similarity	NPC25966
0.9412	High Similarity	NPC232164
0.9412	High Similarity	NPC127218
0.9412	High Similarity	NPC236306
0.9412	High Similarity	NPC471388
0.9403	High Similarity	NPC287745
0.9403	High Similarity	NPC310854
0.9398	High Similarity	NPC175067
0.9398	High Similarity	NPC204215
0.9357	High Similarity	NPC317053
0.9357	High Similarity	NPC324492
0.9357	High Similarity	NPC260397
0.9343	High Similarity	NPC259519
0.9338	High Similarity	NPC102904
0.9338	High Similarity	NPC176051
0.9338	High Similarity	NPC474282
0.9338	High Similarity	NPC326797
0.9338	High Similarity	NPC477938
0.9338	High Similarity	NPC276490
0.9338	High Similarity	NPC103976
0.9338	High Similarity	NPC107551
0.9333	High Similarity	NPC234333
0.9333	High Similarity	NPC34103
0.9333	High Similarity	NPC47398
0.9333	High Similarity	NPC141765
0.9333	High Similarity	NPC165155
0.9333	High Similarity	NPC260898
0.9333	High Similarity	NPC24490
0.9328	High Similarity	NPC475840
0.9328	High Similarity	NPC158331
0.9291	High Similarity	NPC328567
0.9291	High Similarity	NPC16269
0.9291	High Similarity	NPC320671
0.9291	High Similarity	NPC327412
0.9291	High Similarity	NPC320970
0.9291	High Similarity	NPC21776
0.9286	High Similarity	NPC307466
0.9265	High Similarity	NPC16435
0.9265	High Similarity	NPC263367
0.9265	High Similarity	NPC29799
0.9265	High Similarity	NPC265433
0.9265	High Similarity	NPC477939
0.9265	High Similarity	NPC173660
0.9265	High Similarity	NPC177160
0.9265	High Similarity	NPC248727
0.9265	High Similarity	NPC270456
0.9265	High Similarity	NPC54743
0.9265	High Similarity	NPC162659
0.9265	High Similarity	NPC10737
0.9265	High Similarity	NPC156502
0.9265	High Similarity	NPC306441
0.9265	High Similarity	NPC209985
0.9254	High Similarity	NPC35932
0.9254	High Similarity	NPC160991
0.9254	High Similarity	NPC6451
0.9254	High Similarity	NPC7903
0.9254	High Similarity	NPC184447
0.9254	High Similarity	NPC16208
0.9248	High Similarity	NPC214860
0.922	High Similarity	NPC112251
0.9214	High Similarity	NPC470097
0.9214	High Similarity	NPC114119
0.9214	High Similarity	NPC471415
0.9203	High Similarity	NPC291101
0.9203	High Similarity	NPC266197
0.9191	High Similarity	NPC112246
0.9191	High Similarity	NPC112939
0.9191	High Similarity	NPC470356
0.9191	High Similarity	NPC474206
0.9191	High Similarity	NPC61946
0.9191	High Similarity	NPC99572
0.9191	High Similarity	NPC94750
0.9191	High Similarity	NPC195022
0.9191	High Similarity	NPC126409
0.9191	High Similarity	NPC121812
0.9185	High Similarity	NPC105554
0.9179	High Similarity	NPC474356
0.9179	High Similarity	NPC12275
0.9179	High Similarity	NPC309787
0.9179	High Similarity	NPC472597
0.9179	High Similarity	NPC45715
0.9179	High Similarity	NPC474017
0.9179	High Similarity	NPC232275
0.9173	High Similarity	NPC45824
0.9149	High Similarity	NPC181615
0.9137	High Similarity	NPC178054
0.913	High Similarity	NPC22517
0.913	High Similarity	NPC260741
0.913	High Similarity	NPC6369
0.913	High Similarity	NPC70682
0.913	High Similarity	NPC30951
0.9124	High Similarity	NPC230734
0.9124	High Similarity	NPC269091
0.9124	High Similarity	NPC227503
0.9124	High Similarity	NPC470802
0.9124	High Similarity	NPC474639
0.9124	High Similarity	NPC302701
0.9118	High Similarity	NPC187616
0.9118	High Similarity	NPC478085
0.9118	High Similarity	NPC317380
0.9118	High Similarity	NPC106215
0.9118	High Similarity	NPC474478
0.9118	High Similarity	NPC193026
0.9118	High Similarity	NPC170694
0.9118	High Similarity	NPC16485
0.9118	High Similarity	NPC49603
0.9111	High Similarity	NPC470752
0.9111	High Similarity	NPC127624
0.9104	High Similarity	NPC224157
0.9104	High Similarity	NPC469614
0.9104	High Similarity	NPC187998
0.9104	High Similarity	NPC192687
0.9104	High Similarity	NPC77040
0.9104	High Similarity	NPC311680
0.9104	High Similarity	NPC42300
0.9104	High Similarity	NPC174495
0.9104	High Similarity	NPC237169
0.9104	High Similarity	NPC241522
0.9104	High Similarity	NPC153739
0.9104	High Similarity	NPC299221
0.9104	High Similarity	NPC92164
0.9104	High Similarity	NPC472338
0.9104	High Similarity	NPC257582
0.9104	High Similarity	NPC145305
0.9104	High Similarity	NPC242807
0.9104	High Similarity	NPC470624
0.9104	High Similarity	NPC234488
0.9104	High Similarity	NPC64201
0.9104	High Similarity	NPC469612
0.9104	High Similarity	NPC51840
0.9097	High Similarity	NPC472709
0.9097	High Similarity	NPC472710
0.9091	High Similarity	NPC175976
0.9091	High Similarity	NPC473408
0.9091	High Similarity	NPC166584
0.9091	High Similarity	NPC301961
0.9085	High Similarity	NPC226540
0.9078	High Similarity	NPC50250
0.9065	High Similarity	NPC284464
0.9058	High Similarity	NPC46277
0.9058	High Similarity	NPC211549
0.9058	High Similarity	NPC156948
0.9058	High Similarity	NPC86605
0.9058	High Similarity	NPC3072
0.9058	High Similarity	NPC301765
0.9058	High Similarity	NPC474039
0.9051	High Similarity	NPC151224
0.9051	High Similarity	NPC256262
0.9051	High Similarity	NPC164787
0.9044	High Similarity	NPC229442
0.9044	High Similarity	NPC263064
0.9044	High Similarity	NPC11060
0.9044	High Similarity	NPC168059
0.9044	High Similarity	NPC26394
0.9037	High Similarity	NPC42760
0.9037	High Similarity	NPC30043
0.9037	High Similarity	NPC470096
0.9037	High Similarity	NPC470095
0.9037	High Similarity	NPC469613
0.9037	High Similarity	NPC268342
0.9037	High Similarity	NPC469625
0.9037	High Similarity	NPC277804
0.9037	High Similarity	NPC220825
0.9037	High Similarity	NPC268266
0.9034	High Similarity	NPC324517
0.9034	High Similarity	NPC329343
0.9034	High Similarity	NPC321972
0.903	High Similarity	NPC218856
0.903	High Similarity	NPC170844
0.903	High Similarity	NPC285339

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 NPC311530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	880
0.2-0.3	2031
0.3-0.4	2714
0.4-0.5	1551
0.5-0.6	869
0.6-0.7	603
0.7-0.8	144
0.8-0.85	5
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.903	High Similarity	NPD3027	Phase 3
0.8971	High Similarity	NPD1612	Clinical (unspecified phase)
0.8971	High Similarity	NPD1613	Approved
0.8741	High Similarity	NPD1530	Clinical (unspecified phase)
0.8676	High Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2861	Phase 2
0.8273	Intermediate Similarity	NPD4908	Phase 1
0.8162	Intermediate Similarity	NPD1610	Phase 2
0.8156	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1653	Approved
0.8141	Intermediate Similarity	NPD6234	Discontinued
0.8052	Intermediate Similarity	NPD37	Approved
0.8052	Intermediate Similarity	NPD1934	Approved
0.8013	Intermediate Similarity	NPD4965	Approved
0.8013	Intermediate Similarity	NPD4967	Phase 2
0.8013	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.7943	Intermediate Similarity	NPD3018	Phase 2
0.7925	Intermediate Similarity	NPD7199	Phase 2
0.7914	Intermediate Similarity	NPD4749	Approved
0.7902	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7228	Approved
0.7901	Intermediate Similarity	NPD3818	Discontinued
0.7898	Intermediate Similarity	NPD3882	Suspended
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6166	Phase 2
0.7885	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7793	Intermediate Similarity	NPD3620	Phase 2
0.7793	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2983	Phase 2
0.7786	Intermediate Similarity	NPD2982	Phase 2
0.7761	Intermediate Similarity	NPD5283	Phase 1
0.775	Intermediate Similarity	NPD5494	Approved
0.7733	Intermediate Similarity	NPD6674	Discontinued
0.7722	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2981	Phase 2
0.7708	Intermediate Similarity	NPD4625	Phase 3
0.7697	Intermediate Similarity	NPD7074	Phase 3
0.7671	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD3705	Approved
0.7636	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD5844	Phase 1
0.7628	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD228	Approved
0.759	Intermediate Similarity	NPD7472	Approved
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1511	Approved
0.7518	Intermediate Similarity	NPD7157	Approved
0.7518	Intermediate Similarity	NPD6671	Approved
0.7518	Intermediate Similarity	NPD1091	Approved
0.7516	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7483	Intermediate Similarity	NPD6696	Suspended
0.7463	Intermediate Similarity	NPD3022	Approved
0.7463	Intermediate Similarity	NPD3021	Approved
0.7451	Intermediate Similarity	NPD3892	Phase 2
0.744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6797	Phase 2
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7436	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1512	Approved
0.7432	Intermediate Similarity	NPD1558	Phase 1
0.7426	Intermediate Similarity	NPD7843	Approved
0.7415	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7251	Discontinued
0.7396	Intermediate Similarity	NPD7240	Approved
0.7388	Intermediate Similarity	NPD2684	Approved
0.7383	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD3540	Phase 1
0.7368	Intermediate Similarity	NPD5762	Approved
0.7368	Intermediate Similarity	NPD5763	Approved
0.7368	Intermediate Similarity	NPD7266	Discontinued
0.7361	Intermediate Similarity	NPD8651	Approved
0.7358	Intermediate Similarity	NPD4678	Approved
0.7358	Intermediate Similarity	NPD4380	Phase 2
0.7358	Intermediate Similarity	NPD4675	Approved
0.7353	Intermediate Similarity	NPD7808	Phase 3
0.7353	Intermediate Similarity	NPD7549	Discontinued
0.7351	Intermediate Similarity	NPD5588	Approved
0.7313	Intermediate Similarity	NPD290	Approved
0.7305	Intermediate Similarity	NPD1357	Approved
0.7303	Intermediate Similarity	NPD6100	Approved
0.7303	Intermediate Similarity	NPD3539	Phase 1
0.7303	Intermediate Similarity	NPD6099	Approved
0.7301	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4005	Discontinued
0.7294	Intermediate Similarity	NPD6559	Discontinued
0.7292	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2677	Approved
0.7285	Intermediate Similarity	NPD4538	Approved
0.7285	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4536	Approved
0.7284	Intermediate Similarity	NPD5402	Approved
0.7284	Intermediate Similarity	NPD2560	Approved
0.7284	Intermediate Similarity	NPD2563	Approved
0.7283	Intermediate Similarity	NPD4663	Approved
0.7273	Intermediate Similarity	NPD4237	Approved
0.7273	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD4236	Phase 3
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.7267	Intermediate Similarity	NPD5735	Approved
0.7255	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD27	Approved
0.7246	Intermediate Similarity	NPD2489	Approved
0.7244	Intermediate Similarity	NPD5058	Phase 3
0.7241	Intermediate Similarity	NPD7906	Approved
0.7239	Intermediate Similarity	NPD968	Approved
0.7229	Intermediate Similarity	NPD6232	Discontinued
0.7226	Intermediate Similarity	NPD6331	Phase 2
0.7226	Intermediate Similarity	NPD4110	Phase 3
0.7226	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4750	Phase 3
0.7202	Intermediate Similarity	NPD7473	Discontinued
0.72	Intermediate Similarity	NPD2238	Phase 2
0.7197	Intermediate Similarity	NPD7213	Phase 3
0.7197	Intermediate Similarity	NPD7212	Phase 2
0.7195	Intermediate Similarity	NPD7075	Discontinued
0.7186	Intermediate Similarity	NPD2970	Approved
0.7186	Intermediate Similarity	NPD2969	Approved
0.7179	Intermediate Similarity	NPD6190	Approved
0.7178	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3060	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD1375	Discontinued
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7124	Phase 2
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD3051	Approved
0.7124	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5960	Phase 3
0.7124	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2978	Approved
0.7117	Intermediate Similarity	NPD2977	Approved
0.7115	Intermediate Similarity	NPD4628	Phase 3
0.7115	Intermediate Similarity	NPD7466	Approved
0.7115	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7313	Approved
0.711	Intermediate Similarity	NPD7310	Approved
0.711	Intermediate Similarity	NPD7311	Approved
0.711	Intermediate Similarity	NPD4578	Approved
0.711	Intermediate Similarity	NPD4577	Approved
0.711	Intermediate Similarity	NPD7312	Approved
0.7105	Intermediate Similarity	NPD6653	Approved
0.7097	Intermediate Similarity	NPD1549	Phase 2
0.7097	Intermediate Similarity	NPD2424	Discontinued
0.7089	Intermediate Similarity	NPD4357	Discontinued
0.7089	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3496	Discontinued
0.7083	Intermediate Similarity	NPD3926	Phase 2
0.7078	Intermediate Similarity	NPD2161	Phase 2
0.7072	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8053	Approved
0.7069	Intermediate Similarity	NPD7309	Approved
0.7069	Intermediate Similarity	NPD8054	Approved
0.7069	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6798	Discontinued
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7066	Intermediate Similarity	NPD6959	Discontinued
0.7066	Intermediate Similarity	NPD1247	Approved
0.7063	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6111	Discontinued
0.7055	Intermediate Similarity	NPD6801	Discontinued
0.7051	Intermediate Similarity	NPD4162	Approved
0.7044	Intermediate Similarity	NPD4123	Phase 3
0.7039	Intermediate Similarity	NPD230	Phase 1
0.7032	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6002	Phase 3
0.7032	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6004	Phase 3
0.7032	Intermediate Similarity	NPD6005	Phase 3
0.7027	Intermediate Similarity	NPD6584	Phase 3
0.7024	Intermediate Similarity	NPD7229	Phase 3
0.7024	Intermediate Similarity	NPD3787	Discontinued
0.7024	Intermediate Similarity	NPD6071	Discontinued
0.7018	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5846	Approved
0.7014	Intermediate Similarity	NPD6516	Phase 2
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7012	Intermediate Similarity	NPD5773	Approved
0.7012	Intermediate Similarity	NPD7819	Suspended
0.7012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5772	Approved
0.7006	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD7314	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