NPASS Compound

Structure

CID312630 OpenBabel06191716122D 41 46 0 0 1 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7529 -5.8691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9317 -5.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6439 -4.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8052 -4.8705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 5.1962 -3.0000 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 8.3851 -3.3599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -1.0000 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 4.3301 -3.5000 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 3.4641 -3.0000 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 7.0281 -4.2412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1448 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0144 -2.5828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2139 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3865 -3.3076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4538 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 12 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 20 1 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 10 29 1 0 0 0 0 11 17 1 0 0 0 0 11 30 1 0 0 0 0 12 22 1 0 0 0 0 13 2 1 6 0 0 0 13 27 1 0 0 0 0 14 22 1 0 0 0 0 14 25 2 0 0 0 0 15 28 1 0 0 0 0 15 31 1 1 0 0 0 16 23 1 0 0 0 0 16 32 2 0 0 0 0 17 24 1 0 0 0 0 17 33 2 0 0 0 0 18 23 2 0 0 0 0 18 40 1 0 0 0 0 19 24 2 0 0 0 0 19 41 1 0 0 0 0 20 34 2 0 0 0 0 20 38 1 0 0 0 0 21 35 2 0 0 0 0 21 39 1 0 0 0 0 22 26 2 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 29 1 0 0 0 0 27 38 1 6 0 0 0 28 30 1 0 0 0 0 28 39 1 6 0 0 0 29 3 1 6 0 0 0 29 40 1 0 0 0 0 30 4 1 6 0 0 0 30 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.18
Volume:	546.425
LogP:	4.217
LogD:	1.778
LogS:	-4.295
# Rotatable Bonds:	3
TPSA:	165.89
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	5.133
Fsp3:	0.467
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.698
MDCK Permeability:	8.761362551013008e-06
Pgp-inhibitor:	0.166
Pgp-substrate:	0.515
Human Intestinal Absorption (HIA):	0.351
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.359

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	83.31389617919922%
Volume Distribution (VD):	0.84
Pgp-substrate:	5.074996471405029%

ADMET: Metabolism

CYP1A2-inhibitor:	0.166
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.631
CYP2D6-inhibitor:	0.288
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	3.962
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.821
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.568
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.036
Carcinogencity:	0.681
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC312630

Natural Product ID:	NPC312630
*Common Name:**	Monodictyochromone B
IUPAC Name:	(2S)-5-hydroxy-6-[(2R)-5-hydroxy-2-methyl-2-[(2R,3S)-3-methyl-5-oxooxolan-2-yl]-4-oxo-3H-chromen-6-yl]-2-[(2R,3R)-3-hydroxy-5-oxooxolan-2-yl]-2,7-dimethyl-3H-chromen-4-one
Synonyms:
Standard InCHIKey:	YSURVZRGQKOUAG-QXBVHLSASA-N
Standard InCHI:	InChI=1S/C30H30O11/c1-12-7-19-24(17(33)11-30(4,41-19)28-15(31)9-21(35)39-28)26(37)22(12)14-5-6-18-23(25(14)36)16(32)10-29(3,40-18)27-13(2)8-20(34)38-27/h5-7,13,15,27-28,31,36-37H,8-11H2,1-4H3/t13-,15+,27+,28+,29+,30-/m0/s1
SMILES:	O=C1C[C@@H]([C@@H](O1)[C@@]1(C)CC(=O)c2c(O1)ccc(c2O)c1c(C)cc2c(c1O)C(=O)C[C@@](O2)(C)[C@@H]1OC(=O)C[C@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL576579
PubChem CID:	25256842
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO5623	Monodictys putredinis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17291041]
NPO5623	Monodictys putredinis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[18939864]
NPO5623	Monodictys putredinis	Species	n.a.	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
Others	3

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	24.8	uM	PMID[553151]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	=	16500.0	nM	PMID[553151]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	Ratio	=	100.0	n.a.	PMID[553151]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	<=	50.0	%	PMID[553151]
NPT27	Others	Unspecified		IC50	=	7500.0	nM	PMID[553151]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[553151]

☑ 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 NPC312630 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	385
0.1-0.2	1425
0.2-0.3	3036
0.3-0.4	6499
0.4-0.5	11083
0.5-0.6	5466
0.6-0.7	5022
0.7-0.8	7480
0.8-0.85	2098
0.85-0.9	190
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324220
0.9398	High Similarity	NPC477572
0.9398	High Similarity	NPC477571
0.9398	High Similarity	NPC477573
0.9281	High Similarity	NPC241874
0.9217	High Similarity	NPC178173
0.9162	High Similarity	NPC225419
0.9152	High Similarity	NPC473961
0.9146	High Similarity	NPC470810
0.9118	High Similarity	NPC294149
0.9112	High Similarity	NPC472620
0.9075	High Similarity	NPC475656
0.9075	High Similarity	NPC475148
0.9064	High Similarity	NPC475233
0.9053	High Similarity	NPC241387
0.9053	High Similarity	NPC298778
0.9053	High Similarity	NPC251144
0.9048	High Similarity	NPC473094
0.9048	High Similarity	NPC474024
0.9036	High Similarity	NPC472402
0.903	High Similarity	NPC472055
0.9017	High Similarity	NPC475161
0.9017	High Similarity	NPC477860
0.9012	High Similarity	NPC477682
0.9012	High Similarity	NPC477683
0.9006	High Similarity	NPC199533
0.9006	High Similarity	NPC63105
0.9006	High Similarity	NPC470454
0.9006	High Similarity	NPC474345
0.9006	High Similarity	NPC68381
0.9	High Similarity	NPC472584
0.8994	High Similarity	NPC259905
0.8994	High Similarity	NPC473095
0.8994	High Similarity	NPC472619
0.8994	High Similarity	NPC473202
0.8994	High Similarity	NPC473096
0.8988	High Similarity	NPC53640
0.8988	High Similarity	NPC119589
0.8988	High Similarity	NPC178851
0.8976	High Similarity	NPC92589
0.897	High Similarity	NPC186113
0.897	High Similarity	NPC470339
0.896	High Similarity	NPC84494
0.896	High Similarity	NPC245059
0.8953	High Similarity	NPC472661
0.8953	High Similarity	NPC475246
0.8947	High Similarity	NPC213052
0.8947	High Similarity	NPC154986
0.8947	High Similarity	NPC98776
0.8941	High Similarity	NPC120220
0.8941	High Similarity	NPC313304
0.8935	High Similarity	NPC472622
0.8935	High Similarity	NPC476459
0.8916	High Similarity	NPC471976
0.8908	High Similarity	NPC470452
0.8908	High Similarity	NPC164047
0.8908	High Similarity	NPC470448
0.8908	High Similarity	NPC470453
0.8908	High Similarity	NPC208069
0.8896	High Similarity	NPC217447
0.8896	High Similarity	NPC475790
0.8896	High Similarity	NPC87708
0.8895	High Similarity	NPC86809
0.8895	High Similarity	NPC232412
0.8895	High Similarity	NPC3718
0.8895	High Similarity	NPC98667
0.8889	High Similarity	NPC30432
0.8889	High Similarity	NPC76128
0.8889	High Similarity	NPC271385
0.8889	High Similarity	NPC5029
0.8889	High Similarity	NPC111536
0.8882	High Similarity	NPC297195
0.8882	High Similarity	NPC291795
0.8882	High Similarity	NPC207574
0.8882	High Similarity	NPC102810
0.8876	High Similarity	NPC207575
0.8876	High Similarity	NPC43319
0.8876	High Similarity	NPC13481
0.8876	High Similarity	NPC472621
0.8862	High Similarity	NPC30655
0.8862	High Similarity	NPC74854
0.8862	High Similarity	NPC117985
0.8862	High Similarity	NPC45124
0.8862	High Similarity	NPC3629
0.8855	High Similarity	NPC474373
0.8851	High Similarity	NPC299149
0.8851	High Similarity	NPC153578
0.8851	High Similarity	NPC114257
0.8851	High Similarity	NPC277710
0.8848	High Similarity	NPC469936
0.8848	High Similarity	NPC164427
0.8848	High Similarity	NPC129053
0.8848	High Similarity	NPC109967
0.8848	High Similarity	NPC78554
0.8848	High Similarity	NPC321372
0.8848	High Similarity	NPC474609
0.8848	High Similarity	NPC474738
0.8848	High Similarity	NPC475797
0.8844	High Similarity	NPC46958
0.8844	High Similarity	NPC469345
0.8837	High Similarity	NPC472054
0.8834	High Similarity	NPC200773
0.8834	High Similarity	NPC215921
0.8834	High Similarity	NPC72958
0.8834	High Similarity	NPC240768
0.8834	High Similarity	NPC474021
0.8834	High Similarity	NPC70016
0.8834	High Similarity	NPC232645
0.8834	High Similarity	NPC472636
0.8834	High Similarity	NPC474023
0.883	High Similarity	NPC477670
0.8824	High Similarity	NPC218226
0.8824	High Similarity	NPC6588
0.8824	High Similarity	NPC477154
0.8824	High Similarity	NPC117854
0.8817	High Similarity	NPC300053
0.8817	High Similarity	NPC293319
0.8817	High Similarity	NPC25361
0.881	High Similarity	NPC473022
0.881	High Similarity	NPC216752
0.881	High Similarity	NPC15374
0.881	High Similarity	NPC472635
0.8807	High Similarity	NPC472663
0.8807	High Similarity	NPC472662
0.8802	High Similarity	NPC304839
0.8802	High Similarity	NPC220582
0.8788	High Similarity	NPC175192
0.8788	High Similarity	NPC279218
0.8788	High Similarity	NPC477958
0.8788	High Similarity	NPC108937
0.8786	High Similarity	NPC162248
0.878	High Similarity	NPC10807
0.878	High Similarity	NPC56232
0.878	High Similarity	NPC150123
0.878	High Similarity	NPC271681
0.878	High Similarity	NPC473996
0.878	High Similarity	NPC161881
0.878	High Similarity	NPC244583
0.878	High Similarity	NPC273483
0.8779	High Similarity	NPC121333
0.8773	High Similarity	NPC119929
0.8773	High Similarity	NPC179178
0.8773	High Similarity	NPC202595
0.8772	High Similarity	NPC222455
0.8765	High Similarity	NPC170245
0.8765	High Similarity	NPC128293
0.8765	High Similarity	NPC472452
0.8765	High Similarity	NPC173292
0.8765	High Similarity	NPC272502
0.8757	High Similarity	NPC473686
0.8757	High Similarity	NPC87583
0.8757	High Similarity	NPC91288
0.8757	High Similarity	NPC229817
0.8757	High Similarity	NPC475352
0.8757	High Similarity	NPC471286
0.8757	High Similarity	NPC221140
0.8757	High Similarity	NPC124038
0.8757	High Similarity	NPC197168
0.8757	High Similarity	NPC197972
0.8757	High Similarity	NPC186686
0.8757	High Similarity	NPC273959
0.8757	High Similarity	NPC475220
0.875	High Similarity	NPC18380
0.875	High Similarity	NPC472632
0.875	High Similarity	NPC293227
0.875	High Similarity	NPC473717
0.875	High Similarity	NPC473631
0.875	High Similarity	NPC97812
0.875	High Similarity	NPC475662
0.875	High Similarity	NPC137232
0.8743	High Similarity	NPC85121
0.8743	High Similarity	NPC218818
0.8743	High Similarity	NPC473990
0.8743	High Similarity	NPC40583
0.8743	High Similarity	NPC4950
0.8735	High Similarity	NPC20530
0.8735	High Similarity	NPC146211
0.8735	High Similarity	NPC10754
0.8735	High Similarity	NPC208152
0.8735	High Similarity	NPC78492
0.8735	High Similarity	NPC215917
0.8735	High Similarity	NPC471787
0.8735	High Similarity	NPC477674
0.8729	High Similarity	NPC470197
0.8729	High Similarity	NPC470195
0.8729	High Similarity	NPC470196
0.8729	High Similarity	NPC470194
0.8729	High Similarity	NPC470200
0.8729	High Similarity	NPC314687
0.8729	High Similarity	NPC316274
0.8729	High Similarity	NPC282474
0.8729	High Similarity	NPC470198
0.8729	High Similarity	NPC470193
0.8727	High Similarity	NPC326592
0.8727	High Similarity	NPC169990
0.8727	High Similarity	NPC109594
0.8727	High Similarity	NPC135522
0.8727	High Similarity	NPC223701
0.8727	High Similarity	NPC112701
0.8727	High Similarity	NPC469405

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 NPC312630 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	844
0.2-0.3	1776
0.3-0.4	2534
0.4-0.5	2031
0.5-0.6	1034
0.6-0.7	393
0.7-0.8	173
0.8-0.85	26
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD6959	Discontinued
0.8655	High Similarity	NPD7473	Discontinued
0.8621	High Similarity	NPD6559	Discontinued
0.8614	High Similarity	NPD7819	Suspended
0.8588	High Similarity	NPD6232	Discontinued
0.8571	High Similarity	NPD7075	Discontinued
0.8555	High Similarity	NPD5844	Phase 1
0.8545	High Similarity	NPD4380	Phase 2
0.8503	High Similarity	NPD2393	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD5494	Approved
0.8466	Intermediate Similarity	NPD2534	Approved
0.8466	Intermediate Similarity	NPD2533	Approved
0.8466	Intermediate Similarity	NPD2532	Approved
0.8393	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6166	Phase 2
0.8353	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD3749	Approved
0.8343	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD1934	Approved
0.8315	Intermediate Similarity	NPD8312	Approved
0.8315	Intermediate Similarity	NPD8313	Approved
0.8297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD7074	Phase 3
0.8294	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD3818	Discontinued
0.8274	Intermediate Similarity	NPD7411	Suspended
0.8239	Intermediate Similarity	NPD7054	Approved
0.8192	Intermediate Similarity	NPD7472	Approved
0.8182	Intermediate Similarity	NPD7228	Approved
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD6797	Phase 2
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8129	Intermediate Similarity	NPD5402	Approved
0.8107	Intermediate Similarity	NPD6599	Discontinued
0.8101	Intermediate Similarity	NPD7251	Discontinued
0.8092	Intermediate Similarity	NPD6234	Discontinued
0.8081	Intermediate Similarity	NPD3882	Suspended
0.8081	Intermediate Similarity	NPD4966	Approved
0.8081	Intermediate Similarity	NPD4967	Phase 2
0.8081	Intermediate Similarity	NPD4965	Approved
0.807	Intermediate Similarity	NPD2801	Approved
0.8056	Intermediate Similarity	NPD7808	Phase 3
0.8047	Intermediate Similarity	NPD3226	Approved
0.8045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1549	Phase 2
0.7988	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8150	Discontinued
0.7977	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD6799	Approved
0.7955	Intermediate Similarity	NPD5711	Approved
0.7955	Intermediate Similarity	NPD5710	Approved
0.7949	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7783	Phase 2
0.7941	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD8151	Discontinued
0.7929	Intermediate Similarity	NPD5403	Approved
0.7927	Intermediate Similarity	NPD2346	Discontinued
0.7923	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD37	Approved
0.7898	Intermediate Similarity	NPD7199	Phase 2
0.7892	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3750	Approved
0.7892	Intermediate Similarity	NPD4628	Phase 3
0.788	Intermediate Similarity	NPD8434	Phase 2
0.7865	Intermediate Similarity	NPD7435	Discontinued
0.7857	Intermediate Similarity	NPD1511	Approved
0.7824	Intermediate Similarity	NPD920	Approved
0.7811	Intermediate Similarity	NPD5401	Approved
0.7802	Intermediate Similarity	NPD7240	Approved
0.7801	Intermediate Similarity	NPD6781	Approved
0.7801	Intermediate Similarity	NPD6782	Approved
0.7801	Intermediate Similarity	NPD6778	Approved
0.7801	Intermediate Similarity	NPD6780	Approved
0.7801	Intermediate Similarity	NPD6777	Approved
0.7801	Intermediate Similarity	NPD6779	Approved
0.7801	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD3751	Discontinued
0.7765	Intermediate Similarity	NPD1512	Approved
0.7758	Intermediate Similarity	NPD2796	Approved
0.7753	Intermediate Similarity	NPD7229	Phase 3
0.7753	Intermediate Similarity	NPD3787	Discontinued
0.7751	Intermediate Similarity	NPD7390	Discontinued
0.7725	Intermediate Similarity	NPD2800	Approved
0.7709	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7684	Intermediate Similarity	NPD919	Approved
0.7683	Intermediate Similarity	NPD1607	Approved
0.768	Intermediate Similarity	NPD7698	Approved
0.768	Intermediate Similarity	NPD7696	Phase 3
0.768	Intermediate Similarity	NPD7697	Approved
0.7679	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6100	Approved
0.7651	Intermediate Similarity	NPD2935	Discontinued
0.7651	Intermediate Similarity	NPD6099	Approved
0.7651	Intermediate Similarity	NPD1551	Phase 2
0.7641	Intermediate Similarity	NPD8320	Phase 1
0.7641	Intermediate Similarity	NPD8319	Approved
0.7626	Intermediate Similarity	NPD7874	Approved
0.7626	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1243	Approved
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7701	Phase 2
0.759	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2799	Discontinued
0.759	Intermediate Similarity	NPD3748	Approved
0.7588	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1240	Approved
0.7557	Intermediate Similarity	NPD8455	Phase 2
0.7554	Intermediate Similarity	NPD5953	Discontinued
0.7551	Intermediate Similarity	NPD7871	Phase 2
0.7551	Intermediate Similarity	NPD7870	Phase 2
0.7539	Intermediate Similarity	NPD6535	Approved
0.7539	Intermediate Similarity	NPD6534	Approved
0.7538	Intermediate Similarity	NPD6823	Phase 2
0.7514	Intermediate Similarity	NPD3926	Phase 2
0.7513	Intermediate Similarity	NPD7700	Phase 2
0.7513	Intermediate Similarity	NPD7699	Phase 2
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD7801	Approved
0.7485	Intermediate Similarity	NPD4625	Phase 3
0.7475	Intermediate Similarity	NPD7930	Approved
0.7461	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6273	Approved
0.7446	Intermediate Similarity	NPD7286	Phase 2
0.744	Intermediate Similarity	NPD5405	Approved
0.744	Intermediate Similarity	NPD5404	Approved
0.744	Intermediate Similarity	NPD5406	Approved
0.744	Intermediate Similarity	NPD5408	Approved
0.7439	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7458	Discontinued
0.7421	Intermediate Similarity	NPD4287	Approved
0.7419	Intermediate Similarity	NPD7685	Pre-registration
0.7414	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5124	Phase 1
0.741	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2344	Approved
0.7385	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD7003	Approved
0.7368	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5761	Phase 2
0.736	Intermediate Similarity	NPD5760	Phase 2
0.7358	Intermediate Similarity	NPD4360	Phase 2
0.7358	Intermediate Similarity	NPD4363	Phase 3
0.7349	Intermediate Similarity	NPD4060	Phase 1
0.7347	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2438	Suspended
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2313	Discontinued
0.7323	Intermediate Similarity	NPD7680	Approved
0.73	Intermediate Similarity	NPD7584	Approved
0.7297	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7177	Discontinued
0.7296	Intermediate Similarity	NPD8285	Discontinued
0.7294	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6651	Approved
0.726	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1613	Approved
0.7241	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3764	Approved
0.7229	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD6190	Approved
0.7216	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6212	Phase 3
0.7216	Intermediate Similarity	NPD6213	Phase 3
0.7213	Intermediate Similarity	NPD8127	Discontinued
0.7212	Intermediate Similarity	NPD4908	Phase 1
0.7209	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6355	Discontinued
0.7202	Intermediate Similarity	NPD230	Phase 1
0.7193	Intermediate Similarity	NPD6004	Phase 3
0.7193	Intermediate Similarity	NPD6002	Phase 3
0.7193	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6005	Phase 3
0.7193	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1283	Approved
0.7164	Intermediate Similarity	NPD7999	Approved
0.7151	Intermediate Similarity	NPD2424	Discontinued
0.715	Intermediate Similarity	NPD8067	Phase 3
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD4362	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