NPASS Compound

Structure

CID243059 OpenBabel06191716042D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.2227 2.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8100 2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3807 -3.7298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5905 -1.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2386 2.8216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4146 1.1468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5387 -3.2437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2227 -3.2437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7486 -1.7854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5905 -0.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2717 2.7199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4477 1.0452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5387 -2.2715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2227 -2.2715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9066 -1.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7486 0.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0907 1.7301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8762 1.8318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3807 -1.7854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9066 -0.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4861 0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3807 -0.8132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0646 0.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5387 -0.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4371 0.6398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0646 1.1313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6505 -0.7225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1596 1.2904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9066 1.6174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4484 -1.6735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2227 1.6174 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 31 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 0 0 0 0 22 23 1 1 0 0 0 22 24 1 0 0 0 0 23 26 1 6 0 0 0 24 25 2 0 0 0 0 24 27 1 0 0 0 0 25 28 1 0 0 0 0 26 29 2 0 0 0 0 26 31 1 0 0 0 0 27 30 2 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.15
Volume:	450.999
LogP:	4.094
LogD:	3.627
LogS:	-4.711
# Rotatable Bonds:	7
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	3.548
Fsp3:	0.148
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.802
MDCK Permeability:	0.00010179035598412156
Pgp-inhibitor:	0.251
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.184
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.937
Plasma Protein Binding (PPB):	96.06232452392578%
Volume Distribution (VD):	0.652
Pgp-substrate:	5.5766777992248535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.379
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.939
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.551
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	5.04
Half-life (T1/2):	0.025

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.494
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.807
Carcinogencity:	0.321
Eye Corrosion:	0.007
Eye Irritation:	0.236
Respiratory Toxicity:	0.099

Download Data

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

Natural Product: NPC243059

Natural Product ID:	NPC243059
*Common Name:**	Pulveraven A
IUPAC Name:	methyl (2R,3R)-3-[(5Z)-5-benzylidene-4-hydroxy-2-oxofuran-3-yl]-2,3-diphenylpropanoate
Synonyms:
Standard InCHIKey:	DFRUUMWSIQRNGP-CNOHFIPDSA-N
Standard InCHI:	InChI=1S/C27H22O5/c1-31-26(29)23(20-15-9-4-10-16-20)22(19-13-7-3-8-14-19)24-25(28)21(32-27(24)30)17-18-11-5-2-6-12-18/h2-17,22-23,28H,1H3/b21-17-/t22-,23-/m0/s1
SMILES:	COC(=O)[C@@H](c1ccccc1)[C@H](c1ccccc1)C1=C(/C(=C/c2ccccc2)/OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517450
PubChem CID:	54695883
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
NPO23208	Pulveroboletus ravenelii	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542354]
NPO24047	Hydnellum suaveolens	Species	Thelephoraceae	Eukaryota	n.a.	fruit body	n.a.	PMID[16755070]
NPO23543	Hypoxylon fuscum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18928	Heimia myrtifolia	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21616	Cyclosorus striatus	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23208	Pulveroboletus ravenelii	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24003	Argemone alba	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23543	Hypoxylon fuscum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9592.1	Codonopsis foetens subsp. nervosa	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24047	Hydnellum suaveolens	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23280	Cyclamen graecum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28079	Holothuria floridana	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23411	Pseudochlorodesmis furcellata	Species	Bryopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24289	Arctodiaptomus salinus	Species	Diaptomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18928	Heimia myrtifolia	Species	Lythraceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	6.0	ug.mL-1	PMID[543399]

☑ 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 NPC243059 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	240
0.1-0.2	1041
0.2-0.3	2098
0.3-0.4	5809
0.4-0.5	11806
0.5-0.6	10606
0.6-0.7	10543
0.7-0.8	548
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280827
0.8929	High Similarity	NPC281604
0.8673	High Similarity	NPC156648
0.8376	Intermediate Similarity	NPC474689
0.8246	Intermediate Similarity	NPC269644
0.7939	Intermediate Similarity	NPC17567
0.7903	Intermediate Similarity	NPC64340
0.7903	Intermediate Similarity	NPC311091
0.7903	Intermediate Similarity	NPC471033
0.7876	Intermediate Similarity	NPC270654
0.7829	Intermediate Similarity	NPC79608
0.7812	Intermediate Similarity	NPC14141
0.7769	Intermediate Similarity	NPC474314
0.7752	Intermediate Similarity	NPC246166
0.7704	Intermediate Similarity	NPC477896
0.7704	Intermediate Similarity	NPC477893
0.7692	Intermediate Similarity	NPC476033
0.7681	Intermediate Similarity	NPC224491
0.7669	Intermediate Similarity	NPC319995
0.7669	Intermediate Similarity	NPC475478
0.7669	Intermediate Similarity	NPC289415
0.7667	Intermediate Similarity	NPC475282
0.7667	Intermediate Similarity	NPC474364
0.7652	Intermediate Similarity	NPC217431
0.7647	Intermediate Similarity	NPC472551
0.7647	Intermediate Similarity	NPC477251
0.7647	Intermediate Similarity	NPC472545
0.7642	Intermediate Similarity	NPC87069
0.7638	Intermediate Similarity	NPC475804
0.7638	Intermediate Similarity	NPC474222
0.7638	Intermediate Similarity	NPC474223
0.7638	Intermediate Similarity	NPC475827
0.763	Intermediate Similarity	NPC322503
0.763	Intermediate Similarity	NPC38420
0.763	Intermediate Similarity	NPC136608
0.763	Intermediate Similarity	NPC470143
0.7623	Intermediate Similarity	NPC234376
0.7623	Intermediate Similarity	NPC158282
0.76	Intermediate Similarity	NPC128249
0.76	Intermediate Similarity	NPC190298
0.7597	Intermediate Similarity	NPC108286
0.7591	Intermediate Similarity	NPC39549
0.7589	Intermediate Similarity	NPC472556
0.7571	Intermediate Similarity	NPC91703
0.7563	Intermediate Similarity	NPC269457
0.7561	Intermediate Similarity	NPC128368
0.7561	Intermediate Similarity	NPC265002
0.7557	Intermediate Similarity	NPC275576
0.7557	Intermediate Similarity	NPC137416
0.7538	Intermediate Similarity	NPC85511
0.7537	Intermediate Similarity	NPC291419
0.7537	Intermediate Similarity	NPC60825
0.7537	Intermediate Similarity	NPC285361
0.7536	Intermediate Similarity	NPC473301
0.7534	Intermediate Similarity	NPC267091
0.7518	Intermediate Similarity	NPC309056
0.75	Intermediate Similarity	NPC988
0.75	Intermediate Similarity	NPC88255
0.75	Intermediate Similarity	NPC136994
0.75	Intermediate Similarity	NPC169913
0.75	Intermediate Similarity	NPC51174
0.75	Intermediate Similarity	NPC179411
0.75	Intermediate Similarity	NPC289432
0.75	Intermediate Similarity	NPC473423
0.7482	Intermediate Similarity	NPC472547
0.7482	Intermediate Similarity	NPC171207
0.7482	Intermediate Similarity	NPC97667
0.7482	Intermediate Similarity	NPC100913
0.7482	Intermediate Similarity	NPC275592
0.7481	Intermediate Similarity	NPC295664
0.7481	Intermediate Similarity	NPC233692
0.7481	Intermediate Similarity	NPC288945
0.7466	Intermediate Similarity	NPC243891
0.7464	Intermediate Similarity	NPC27721
0.7463	Intermediate Similarity	NPC472388
0.7463	Intermediate Similarity	NPC64111
0.7463	Intermediate Similarity	NPC208536
0.7463	Intermediate Similarity	NPC473443
0.7462	Intermediate Similarity	NPC474254
0.7462	Intermediate Similarity	NPC474159
0.7462	Intermediate Similarity	NPC472703
0.746	Intermediate Similarity	NPC212891
0.7447	Intermediate Similarity	NPC284957
0.7442	Intermediate Similarity	NPC144547
0.744	Intermediate Similarity	NPC210092
0.744	Intermediate Similarity	NPC474408
0.744	Intermediate Similarity	NPC221275
0.7436	Intermediate Similarity	NPC476042
0.7429	Intermediate Similarity	NPC87448
0.7429	Intermediate Similarity	NPC16912
0.7429	Intermediate Similarity	NPC41481
0.7429	Intermediate Similarity	NPC242355
0.7429	Intermediate Similarity	NPC472576
0.7429	Intermediate Similarity	NPC27377
0.7429	Intermediate Similarity	NPC266374
0.7429	Intermediate Similarity	NPC213567
0.7429	Intermediate Similarity	NPC97947
0.7429	Intermediate Similarity	NPC291599
0.7429	Intermediate Similarity	NPC77493
0.7429	Intermediate Similarity	NPC118080
0.7424	Intermediate Similarity	NPC236405
0.7424	Intermediate Similarity	NPC88403
0.7422	Intermediate Similarity	NPC204784
0.7419	Intermediate Similarity	NPC17693
0.7419	Intermediate Similarity	NPC272524
0.7415	Intermediate Similarity	NPC270268
0.741	Intermediate Similarity	NPC475195
0.7407	Intermediate Similarity	NPC72915
0.7407	Intermediate Similarity	NPC2989
0.7407	Intermediate Similarity	NPC472361
0.7405	Intermediate Similarity	NPC140118
0.7405	Intermediate Similarity	NPC471466
0.7405	Intermediate Similarity	NPC138798
0.7405	Intermediate Similarity	NPC472704
0.7405	Intermediate Similarity	NPC469742
0.7405	Intermediate Similarity	NPC51079
0.7405	Intermediate Similarity	NPC12881
0.7402	Intermediate Similarity	NPC228318
0.7402	Intermediate Similarity	NPC325295
0.7402	Intermediate Similarity	NPC469574
0.7402	Intermediate Similarity	NPC76308
0.7402	Intermediate Similarity	NPC45794
0.7395	Intermediate Similarity	NPC91820
0.7395	Intermediate Similarity	NPC82426
0.7395	Intermediate Similarity	NPC329556
0.7394	Intermediate Similarity	NPC95810
0.7394	Intermediate Similarity	NPC475759
0.7394	Intermediate Similarity	NPC476974
0.7394	Intermediate Similarity	NPC472570
0.7394	Intermediate Similarity	NPC472573
0.7394	Intermediate Similarity	NPC11685
0.7394	Intermediate Similarity	NPC470152
0.7394	Intermediate Similarity	NPC163719
0.7394	Intermediate Similarity	NPC95265
0.7394	Intermediate Similarity	NPC475122
0.7394	Intermediate Similarity	NPC472569
0.7394	Intermediate Similarity	NPC70716
0.7394	Intermediate Similarity	NPC125106
0.7394	Intermediate Similarity	NPC188865
0.7394	Intermediate Similarity	NPC57628
0.7394	Intermediate Similarity	NPC241951
0.7394	Intermediate Similarity	NPC25768
0.7391	Intermediate Similarity	NPC202729
0.7391	Intermediate Similarity	NPC472372
0.7391	Intermediate Similarity	NPC472374
0.7388	Intermediate Similarity	NPC225103
0.7388	Intermediate Similarity	NPC167463
0.7388	Intermediate Similarity	NPC2596
0.7388	Intermediate Similarity	NPC79332
0.7388	Intermediate Similarity	NPC46192
0.7385	Intermediate Similarity	NPC167323
0.7385	Intermediate Similarity	NPC475328
0.7385	Intermediate Similarity	NPC269923
0.7377	Intermediate Similarity	NPC40178
0.7376	Intermediate Similarity	NPC182869
0.7376	Intermediate Similarity	NPC472546
0.7376	Intermediate Similarity	NPC9218
0.7372	Intermediate Similarity	NPC48929
0.7372	Intermediate Similarity	NPC311492
0.7372	Intermediate Similarity	NPC310662
0.7372	Intermediate Similarity	NPC28836
0.7372	Intermediate Similarity	NPC474608
0.7372	Intermediate Similarity	NPC202743
0.7368	Intermediate Similarity	NPC171007
0.7368	Intermediate Similarity	NPC253681
0.7368	Intermediate Similarity	NPC190849
0.7364	Intermediate Similarity	NPC232958
0.7364	Intermediate Similarity	NPC77000
0.7364	Intermediate Similarity	NPC238861
0.7361	Intermediate Similarity	NPC281717
0.736	Intermediate Similarity	NPC307651
0.736	Intermediate Similarity	NPC153053
0.7357	Intermediate Similarity	NPC473440
0.7357	Intermediate Similarity	NPC90614
0.7355	Intermediate Similarity	NPC136962
0.7353	Intermediate Similarity	NPC475493
0.7353	Intermediate Similarity	NPC233860
0.7353	Intermediate Similarity	NPC209851
0.7353	Intermediate Similarity	NPC80599
0.7353	Intermediate Similarity	NPC239358
0.735	Intermediate Similarity	NPC154517
0.7343	Intermediate Similarity	NPC472568
0.7343	Intermediate Similarity	NPC472572
0.7343	Intermediate Similarity	NPC200471
0.7343	Intermediate Similarity	NPC158663
0.7343	Intermediate Similarity	NPC471104
0.7343	Intermediate Similarity	NPC70403
0.7343	Intermediate Similarity	NPC470159
0.7343	Intermediate Similarity	NPC174982
0.7343	Intermediate Similarity	NPC202391
0.7343	Intermediate Similarity	NPC476973
0.7343	Intermediate Similarity	NPC470157
0.7343	Intermediate Similarity	NPC184817
0.7343	Intermediate Similarity	NPC472575
0.7343	Intermediate Similarity	NPC296659
0.7343	Intermediate Similarity	NPC177940
0.7343	Intermediate Similarity	NPC469349
0.7343	Intermediate Similarity	NPC171525
0.7343	Intermediate Similarity	NPC472571
0.7343	Intermediate Similarity	NPC96903

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 NPC243059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	730
0.2-0.3	1166
0.3-0.4	2534
0.4-0.5	2636
0.5-0.6	1351
0.6-0.7	481
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8407	Intermediate Similarity	NPD5909	Discontinued
0.8017	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD2067	Discontinued
0.7727	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD2629	Approved
0.7537	Intermediate Similarity	NPD3764	Approved
0.7447	Intermediate Similarity	NPD4628	Phase 3
0.7436	Intermediate Similarity	NPD7798	Approved
0.7436	Intermediate Similarity	NPD2066	Phase 3
0.7407	Intermediate Similarity	NPD3268	Approved
0.7395	Intermediate Similarity	NPD1930	Approved
0.7395	Intermediate Similarity	NPD1929	Approved
0.7395	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4198	Discontinued
0.7376	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1608	Approved
0.7328	Intermediate Similarity	NPD1989	Approved
0.7304	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5951	Approved
0.7299	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2797	Approved
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD5048	Discontinued
0.7258	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6647	Phase 2
0.7246	Intermediate Similarity	NPD6355	Discontinued
0.7231	Intermediate Similarity	NPD17	Approved
0.7231	Intermediate Similarity	NPD5305	Approved
0.7231	Intermediate Similarity	NPD5306	Approved
0.7206	Intermediate Similarity	NPD7008	Discontinued
0.7176	Intermediate Similarity	NPD4106	Approved
0.7176	Intermediate Similarity	NPD4135	Approved
0.7176	Intermediate Similarity	NPD4136	Approved
0.7164	Intermediate Similarity	NPD3266	Approved
0.7164	Intermediate Similarity	NPD3267	Approved
0.7154	Intermediate Similarity	NPD4102	Approved
0.7154	Intermediate Similarity	NPD4105	Approved
0.7143	Intermediate Similarity	NPD1238	Approved
0.7123	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4806	Approved
0.7121	Intermediate Similarity	NPD4807	Approved
0.7101	Intermediate Similarity	NPD6233	Phase 2
0.7099	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2182	Approved
0.7094	Intermediate Similarity	NPD1693	Approved
0.7068	Intermediate Similarity	NPD6637	Approved
0.7043	Intermediate Similarity	NPD1089	Approved
0.7043	Intermediate Similarity	NPD1086	Approved
0.7043	Intermediate Similarity	NPD1090	Approved
0.7008	Intermediate Similarity	NPD7094	Approved
0.7008	Intermediate Similarity	NPD6858	Approved
0.7	Intermediate Similarity	NPD2347	Approved
0.6992	Remote Similarity	NPD6287	Discontinued
0.6985	Remote Similarity	NPD2798	Approved
0.6983	Remote Similarity	NPD1239	Approved
0.6975	Remote Similarity	NPD1564	Approved
0.6975	Remote Similarity	NPD1566	Phase 3
0.6975	Remote Similarity	NPD1565	Approved
0.6966	Remote Similarity	NPD7003	Approved
0.6966	Remote Similarity	NPD8166	Discontinued
0.6963	Remote Similarity	NPD3225	Approved
0.696	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7095	Approved
0.6957	Remote Similarity	NPD800	Approved
0.6949	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9545	Approved
0.6934	Remote Similarity	NPD5204	Approved
0.6933	Remote Similarity	NPD7458	Discontinued
0.693	Remote Similarity	NPD1087	Approved
0.6929	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1088	Approved
0.6918	Remote Similarity	NPD6190	Approved
0.6917	Remote Similarity	NPD5926	Approved
0.6917	Remote Similarity	NPD9495	Approved
0.6913	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD164	Approved
0.6897	Remote Similarity	NPD3672	Approved
0.6897	Remote Similarity	NPD3673	Approved
0.6885	Remote Similarity	NPD1932	Approved
0.6884	Remote Similarity	NPD4620	Approved
0.6884	Remote Similarity	NPD5203	Approved
0.6884	Remote Similarity	NPD5201	Approved
0.6884	Remote Similarity	NPD4617	Approved
0.6884	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1202	Approved
0.6864	Remote Similarity	NPD1563	Approved
0.6853	Remote Similarity	NPD7033	Discontinued
0.6853	Remote Similarity	NPD2799	Discontinued
0.6842	Remote Similarity	NPD5125	Phase 3
0.6842	Remote Similarity	NPD5126	Approved
0.6842	Remote Similarity	NPD7411	Suspended
0.6838	Remote Similarity	NPD5667	Approved
0.6838	Remote Similarity	NPD1283	Approved
0.6825	Remote Similarity	NPD2329	Discontinued
0.6824	Remote Similarity	NPD6799	Approved
0.6821	Remote Similarity	NPD3226	Approved
0.6809	Remote Similarity	NPD5119	Approved
0.6809	Remote Similarity	NPD5121	Approved
0.6809	Remote Similarity	NPD5120	Approved
0.68	Remote Similarity	NPD6685	Approved
0.6786	Remote Similarity	NPD2313	Discontinued
0.6786	Remote Similarity	NPD4621	Approved
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4619	Approved
0.6776	Remote Similarity	NPD6599	Discontinued
0.6774	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1237	Approved
0.6759	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7236	Approved
0.6753	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5535	Approved
0.6741	Remote Similarity	NPD1281	Approved
0.6739	Remote Similarity	NPD5647	Approved
0.6738	Remote Similarity	NPD7715	Approved
0.6738	Remote Similarity	NPD4062	Phase 3
0.6738	Remote Similarity	NPD6663	Approved
0.6738	Remote Similarity	NPD7714	Approved
0.6736	Remote Similarity	NPD4308	Phase 3
0.6735	Remote Similarity	NPD3750	Approved
0.6733	Remote Similarity	NPD6273	Approved
0.6731	Remote Similarity	NPD7075	Discontinued
0.6726	Remote Similarity	NPD9491	Approved
0.6719	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1876	Approved
0.6712	Remote Similarity	NPD5958	Discontinued
0.6711	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7199	Phase 2
0.6694	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7741	Discontinued
0.6692	Remote Similarity	NPD2652	Approved
0.6692	Remote Similarity	NPD1894	Discontinued
0.6692	Remote Similarity	NPD2650	Approved
0.6691	Remote Similarity	NPD3661	Approved
0.6691	Remote Similarity	NPD4878	Approved
0.6691	Remote Similarity	NPD5736	Approved
0.6691	Remote Similarity	NPD3663	Approved
0.6691	Remote Similarity	NPD3972	Approved
0.6691	Remote Similarity	NPD3664	Approved
0.6691	Remote Similarity	NPD3662	Phase 3
0.669	Remote Similarity	NPD6310	Approved
0.669	Remote Similarity	NPD2979	Phase 3
0.669	Remote Similarity	NPD2438	Suspended
0.669	Remote Similarity	NPD6311	Approved
0.669	Remote Similarity	NPD2935	Discontinued
0.669	Remote Similarity	NPD6309	Approved
0.669	Remote Similarity	NPD4060	Phase 1
0.6689	Remote Similarity	NPD5403	Approved
0.6688	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD4576	Approved
0.6667	Remote Similarity	NPD5347	Phase 2
0.6667	Remote Similarity	NPD4574	Approved
0.6667	Remote Similarity	NPD5346	Phase 2
0.6667	Remote Similarity	NPD969	Suspended
0.6646	Remote Similarity	NPD7473	Discontinued
0.6645	Remote Similarity	NPD8455	Phase 2
0.6644	Remote Similarity	NPD6002	Phase 3
0.6644	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6005	Phase 3
0.6644	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6004	Phase 3
0.6644	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2346	Discontinued
0.6643	Remote Similarity	NPD4340	Discontinued
0.6643	Remote Similarity	NPD6832	Phase 2
0.6642	Remote Similarity	NPD5585	Approved
0.6641	Remote Similarity	NPD4234	Approved
0.6641	Remote Similarity	NPD5237	Approved
0.6641	Remote Similarity	NPD5235	Approved
0.6641	Remote Similarity	NPD5240	Approved
0.6641	Remote Similarity	NPD4233	Approved
0.6641	Remote Similarity	NPD5236	Approved
0.6641	Remote Similarity	NPD5239	Approved
0.6638	Remote Similarity	NPD1282	Approved
0.6625	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4110	Phase 3
0.6621	Remote Similarity	NPD3748	Approved
0.662	Remote Similarity	NPD8032	Phase 2
0.6619	Remote Similarity	NPD6085	Phase 2
0.6619	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD2788	Approved
0.661	Remote Similarity	NPD9256	Approved
0.661	Remote Similarity	NPD9258	Approved
0.6603	Remote Similarity	NPD3817	Phase 2
0.6601	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD4534	Discontinued
0.6599	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6653	Approved
0.6593	Remote Similarity	NPD3019	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