NPASS Compound

Structure

CID124313 OpenBabel06191715482D 25 29 0 0 0 0 0 0 0 0999 V2000 -4.2602 1.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0333 1.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1984 -3.6878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9984 -4.1489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6091 -2.2892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4257 -0.9159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6346 0.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9192 0.0966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1936 -2.7550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4380 0.0190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6099 -1.3727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8188 0.0403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6082 -1.3661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9940 -2.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8064 -0.8946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0012 -1.3594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8088 -2.7581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6140 -2.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1922 -0.9040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7988 -3.6868 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4194 -2.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2480 0.4724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0211 0.5150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2951 -0.7477 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 20 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 12 2 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 14 1 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 19 2 0 0 0 0 13 24 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 21 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.08
Volume:	325.618
LogP:	3.686
LogD:	2.905
LogS:	-6.71
# Rotatable Bonds:	2
TPSA:	66.88
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	2.713
Fsp3:	0.158
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:	-4.968
MDCK Permeability:	3.247049608035013e-05
Pgp-inhibitor:	0.671
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	90.06824493408203%
Volume Distribution (VD):	0.814
Pgp-substrate:	3.358865976333618%

ADMET: Metabolism

CYP1A2-inhibitor:	0.868
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.402
CYP2C9-inhibitor:	0.651
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.511
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	10.95
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.35
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.825
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.04
Carcinogencity:	0.925
Eye Corrosion:	0.004
Eye Irritation:	0.24
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC124313

Natural Product ID:	NPC124313
*Common Name:**	Oxodiscoguattine
IUPAC Name:	n.a.
Synonyms:	Oxodiscoguattine
Standard InCHIKey:	UMPOYLHHDRUHOO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13NO5/c1-22-10-6-11-15(12(7-10)23-2)16-14-9(3-4-20-17(14)18(11)21)5-13-19(16)25-8-24-13/h3-7H,8H2,1-2H3
SMILES:	COc1cc(OC)cc2c1c1c3OCOc3cc3c1c(C2=O)ncc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390615
PubChem CID:	16126692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	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	2
Others	3

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells	IC50	=	2150.0	nM	PMID[557040]
NPT27	Others	Unspecified	CC50	=	32300.0	nM	PMID[557040]
NPT2	Others	Unspecified	IC50	=	3580.0	nM	PMID[557040]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	9.0	n.a.	PMID[557040]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	15.0	n.a.	PMID[557040]

☑ 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 NPC124313 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	587
0.1-0.2	2655
0.2-0.3	10115
0.3-0.4	7159
0.4-0.5	8161
0.5-0.6	11702
0.6-0.7	1986
0.7-0.8	274
0.8-0.85	37
0.85-0.9	3
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC207283
0.9907	High Similarity	NPC84164
0.9773	High Similarity	NPC183537
0.9721	High Similarity	NPC182907
0.9721	High Similarity	NPC189903
0.9674	High Similarity	NPC108342
0.9595	High Similarity	NPC77878
0.9581	High Similarity	NPC22481
0.9537	High Similarity	NPC90875
0.9535	High Similarity	NPC233334
0.9495	High Similarity	NPC166722
0.9442	High Similarity	NPC278525
0.9409	High Similarity	NPC210296
0.9352	High Similarity	NPC24019
0.9324	High Similarity	NPC15406
0.9163	High Similarity	NPC210434
0.8811	High Similarity	NPC119134
0.875	High Similarity	NPC146976
0.8704	High Similarity	NPC236668
0.8486	Intermediate Similarity	NPC251160
0.8428	Intermediate Similarity	NPC253675
0.8394	Intermediate Similarity	NPC470020
0.8311	Intermediate Similarity	NPC122463
0.827	Intermediate Similarity	NPC270515
0.8174	Intermediate Similarity	NPC478045
0.8161	Intermediate Similarity	NPC235076
0.8145	Intermediate Similarity	NPC188420
0.8114	Intermediate Similarity	NPC322482
0.8065	Intermediate Similarity	NPC477019
0.8053	Intermediate Similarity	NPC23614
0.8053	Intermediate Similarity	NPC100079
0.8036	Intermediate Similarity	NPC149471
0.8036	Intermediate Similarity	NPC271215
0.8018	Intermediate Similarity	NPC46451
0.8008	Intermediate Similarity	NPC134637
0.7991	Intermediate Similarity	NPC296482
0.7991	Intermediate Similarity	NPC53069
0.7991	Intermediate Similarity	NPC202768
0.7982	Intermediate Similarity	NPC234197
0.7982	Intermediate Similarity	NPC174049
0.7965	Intermediate Similarity	NPC470018
0.7931	Intermediate Similarity	NPC74575
0.7928	Intermediate Similarity	NPC313189
0.7918	Intermediate Similarity	NPC318068
0.7913	Intermediate Similarity	NPC118121
0.7911	Intermediate Similarity	NPC96405
0.7911	Intermediate Similarity	NPC171409
0.7904	Intermediate Similarity	NPC54066
0.7895	Intermediate Similarity	NPC204446
0.7884	Intermediate Similarity	NPC107123
0.7871	Intermediate Similarity	NPC132385
0.7854	Intermediate Similarity	NPC129897
0.7848	Intermediate Similarity	NPC135549
0.7824	Intermediate Similarity	NPC133140
0.7824	Intermediate Similarity	NPC195268
0.7823	Intermediate Similarity	NPC191489
0.7817	Intermediate Similarity	NPC473822
0.7797	Intermediate Similarity	NPC49547
0.7773	Intermediate Similarity	NPC470017
0.7763	Intermediate Similarity	NPC55470
0.7759	Intermediate Similarity	NPC216612
0.7755	Intermediate Similarity	NPC302807
0.7755	Intermediate Similarity	NPC137353
0.7741	Intermediate Similarity	NPC470022
0.7698	Intermediate Similarity	NPC88923
0.7698	Intermediate Similarity	NPC315634
0.7698	Intermediate Similarity	NPC100734
0.7679	Intermediate Similarity	NPC16452
0.7679	Intermediate Similarity	NPC36229
0.7679	Intermediate Similarity	NPC476581
0.7669	Intermediate Similarity	NPC246381
0.7633	Intermediate Similarity	NPC1608
0.7615	Intermediate Similarity	NPC96584
0.7615	Intermediate Similarity	NPC255800
0.7613	Intermediate Similarity	NPC476578
0.7613	Intermediate Similarity	NPC4071
0.7613	Intermediate Similarity	NPC476582
0.7605	Intermediate Similarity	NPC201508
0.7604	Intermediate Similarity	NPC474009
0.7551	Intermediate Similarity	NPC208522
0.7545	Intermediate Similarity	NPC31930
0.7533	Intermediate Similarity	NPC193238
0.7529	Intermediate Similarity	NPC470042
0.7523	Intermediate Similarity	NPC224928
0.75	Intermediate Similarity	NPC217554
0.75	Intermediate Similarity	NPC471004
0.75	Intermediate Similarity	NPC284685
0.7489	Intermediate Similarity	NPC127085
0.748	Intermediate Similarity	NPC284141
0.7478	Intermediate Similarity	NPC220337
0.7469	Intermediate Similarity	NPC72905
0.7458	Intermediate Similarity	NPC477788
0.7458	Intermediate Similarity	NPC476999
0.7456	Intermediate Similarity	NPC308943
0.7447	Intermediate Similarity	NPC469439
0.7446	Intermediate Similarity	NPC202605
0.7446	Intermediate Similarity	NPC112206
0.7439	Intermediate Similarity	NPC142385
0.7435	Intermediate Similarity	NPC290689
0.7421	Intermediate Similarity	NPC13603
0.7418	Intermediate Similarity	NPC11408
0.7411	Intermediate Similarity	NPC23080
0.7411	Intermediate Similarity	NPC193906
0.7402	Intermediate Similarity	NPC473833
0.7388	Intermediate Similarity	NPC168922
0.7388	Intermediate Similarity	NPC41501
0.7388	Intermediate Similarity	NPC253482
0.7381	Intermediate Similarity	NPC475301
0.7381	Intermediate Similarity	NPC326930
0.7381	Intermediate Similarity	NPC53255
0.7381	Intermediate Similarity	NPC85879
0.7378	Intermediate Similarity	NPC5374
0.7373	Intermediate Similarity	NPC282346
0.7368	Intermediate Similarity	NPC475648
0.7364	Intermediate Similarity	NPC473506
0.7353	Intermediate Similarity	NPC94842
0.7344	Intermediate Similarity	NPC328928
0.7333	Intermediate Similarity	NPC477787
0.7333	Intermediate Similarity	NPC328186
0.7333	Intermediate Similarity	NPC475631
0.7333	Intermediate Similarity	NPC122968
0.7333	Intermediate Similarity	NPC87152
0.7333	Intermediate Similarity	NPC476110
0.7333	Intermediate Similarity	NPC228377
0.7333	Intermediate Similarity	NPC475600
0.7331	Intermediate Similarity	NPC148409
0.7316	Intermediate Similarity	NPC46990
0.7314	Intermediate Similarity	NPC316841
0.7314	Intermediate Similarity	NPC475303
0.7314	Intermediate Similarity	NPC292416
0.7314	Intermediate Similarity	NPC475596
0.7314	Intermediate Similarity	NPC473689
0.7308	Intermediate Similarity	NPC4421
0.7304	Intermediate Similarity	NPC222561
0.7303	Intermediate Similarity	NPC475644
0.7303	Intermediate Similarity	NPC471977
0.7303	Intermediate Similarity	NPC471190
0.7303	Intermediate Similarity	NPC476997
0.7303	Intermediate Similarity	NPC470486
0.7295	Intermediate Similarity	NPC475406
0.7288	Intermediate Similarity	NPC473115
0.7288	Intermediate Similarity	NPC158020
0.7288	Intermediate Similarity	NPC473089
0.7288	Intermediate Similarity	NPC6576
0.7288	Intermediate Similarity	NPC195120
0.7288	Intermediate Similarity	NPC212768
0.7288	Intermediate Similarity	NPC75600
0.7284	Intermediate Similarity	NPC244839
0.7284	Intermediate Similarity	NPC320324
0.7284	Intermediate Similarity	NPC30456
0.7284	Intermediate Similarity	NPC319880
0.7277	Intermediate Similarity	NPC146724
0.7276	Intermediate Similarity	NPC471978
0.7273	Intermediate Similarity	NPC476998
0.7273	Intermediate Similarity	NPC476996
0.7269	Intermediate Similarity	NPC477903
0.7265	Intermediate Similarity	NPC327904
0.7265	Intermediate Similarity	NPC38959
0.7265	Intermediate Similarity	NPC474594
0.7259	Intermediate Similarity	NPC471979
0.7257	Intermediate Similarity	NPC71124
0.7254	Intermediate Similarity	NPC237702
0.7252	Intermediate Similarity	NPC312531
0.7248	Intermediate Similarity	NPC206201
0.7244	Intermediate Similarity	NPC303374
0.7243	Intermediate Similarity	NPC217176
0.7236	Intermediate Similarity	NPC476995
0.7232	Intermediate Similarity	NPC254957
0.7231	Intermediate Similarity	NPC476994
0.7227	Intermediate Similarity	NPC118154
0.7227	Intermediate Similarity	NPC157983
0.7224	Intermediate Similarity	NPC327769
0.7224	Intermediate Similarity	NPC35208
0.7218	Intermediate Similarity	NPC148889
0.7217	Intermediate Similarity	NPC164374
0.7217	Intermediate Similarity	NPC210256
0.7217	Intermediate Similarity	NPC137929
0.7216	Intermediate Similarity	NPC120513
0.7216	Intermediate Similarity	NPC472589
0.7215	Intermediate Similarity	NPC87560
0.7211	Intermediate Similarity	NPC324619
0.7211	Intermediate Similarity	NPC475315
0.7208	Intermediate Similarity	NPC76565
0.7208	Intermediate Similarity	NPC250807
0.7208	Intermediate Similarity	NPC57797
0.7208	Intermediate Similarity	NPC122436
0.7198	Intermediate Similarity	NPC89549
0.7195	Intermediate Similarity	NPC204385
0.7191	Intermediate Similarity	NPC232225
0.719	Intermediate Similarity	NPC211920
0.719	Intermediate Similarity	NPC146824
0.7185	Intermediate Similarity	NPC84815
0.7185	Intermediate Similarity	NPC301368
0.7178	Intermediate Similarity	NPC473850
0.7178	Intermediate Similarity	NPC328154
0.7178	Intermediate Similarity	NPC475498
0.7178	Intermediate Similarity	NPC475137
0.7176	Intermediate Similarity	NPC473639
0.7176	Intermediate Similarity	NPC101312
0.7174	Intermediate Similarity	NPC207971

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 NPC124313 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	661
0.2-0.3	985
0.3-0.4	1792
0.4-0.5	2637
0.5-0.6	2069
0.6-0.7	616
0.7-0.8	44
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
0.8018	Intermediate Similarity	NPD3763	Approved
0.7991	Intermediate Similarity	NPD3816	Phase 1
0.7991	Intermediate Similarity	NPD3815	Phase 1
0.7899	Intermediate Similarity	NPD7885	Phase 2
0.7899	Intermediate Similarity	NPD7886	Phase 2
0.7837	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3922	Approved
0.7824	Intermediate Similarity	NPD3921	Approved
0.7824	Intermediate Similarity	NPD3924	Approved
0.7824	Intermediate Similarity	NPD3923	Approved
0.7823	Intermediate Similarity	NPD7708	Approved
0.7787	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1483	Discontinued
0.7746	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7803	Approved
0.7649	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8091	Phase 3
0.75	Intermediate Similarity	NPD7956	Approved
0.75	Intermediate Similarity	NPD7955	Approved
0.7446	Intermediate Similarity	NPD7069	Discontinued
0.7429	Intermediate Similarity	NPD6790	Phase 1
0.7414	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7417	Discontinued
0.7355	Intermediate Similarity	NPD4885	Approved
0.7344	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6494	Phase 2
0.7315	Intermediate Similarity	NPD3920	Phase 2
0.7306	Intermediate Similarity	NPD5805	Approved
0.7291	Intermediate Similarity	NPD5482	Discontinued
0.7227	Intermediate Similarity	NPD6242	Discontinued
0.72	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5488	Discontinued
0.7169	Intermediate Similarity	NPD3386	Phase 2
0.7154	Intermediate Similarity	NPD6964	Approved
0.7154	Intermediate Similarity	NPD6963	Approved
0.7149	Intermediate Similarity	NPD5866	Approved
0.7143	Intermediate Similarity	NPD6568	Discontinued
0.7143	Intermediate Similarity	NPD7395	Discontinued
0.7085	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6727	Phase 2
0.7054	Intermediate Similarity	NPD7169	Suspended
0.7045	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4989	Phase 2
0.7	Intermediate Similarity	NPD4429	Discontinued
0.6996	Remote Similarity	NPD4889	Approved
0.6996	Remote Similarity	NPD7673	Phase 3
0.6992	Remote Similarity	NPD4952	Phase 3
0.6984	Remote Similarity	NPD6716	Phase 1
0.6983	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3217	Phase 2
0.6972	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6969	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4846	Phase 2
0.6958	Remote Similarity	NPD5450	Discontinued
0.6958	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8479	Phase 2
0.6937	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5429	Discontinued
0.6935	Remote Similarity	NPD6530	Approved
0.6935	Remote Similarity	NPD6531	Approved
0.6923	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6745	Discontinued
0.6908	Remote Similarity	NPD4373	Phase 2
0.6902	Remote Similarity	NPD8468	Phase 2
0.6898	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7588	Discontinued
0.687	Remote Similarity	NPD6228	Discontinued
0.686	Remote Similarity	NPD3354	Phase 2
0.686	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6361	Phase 2
0.6855	Remote Similarity	NPD5022	Discontinued
0.6853	Remote Similarity	NPD3006	Discontinued
0.685	Remote Similarity	NPD6517	Phase 3
0.6849	Remote Similarity	NPD5914	Approved
0.6849	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3259	Approved
0.6838	Remote Similarity	NPD5005	Approved
0.6838	Remote Similarity	NPD5006	Approved
0.6835	Remote Similarity	NPD5658	Approved
0.6833	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4418	Discontinued
0.6816	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7654	Discontinued
0.6814	Remote Similarity	NPD4375	Approved
0.6809	Remote Similarity	NPD5513	Phase 2
0.6802	Remote Similarity	NPD7426	Phase 1
0.6802	Remote Similarity	NPD3263	Phase 3
0.6797	Remote Similarity	NPD6230	Discontinued
0.6791	Remote Similarity	NPD5459	Phase 2
0.6789	Remote Similarity	NPD7278	Phase 2
0.6789	Remote Similarity	NPD7279	Phase 2
0.6787	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5891	Approved
0.678	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7859	Phase 2
0.6765	Remote Similarity	NPD4859	Phase 1
0.6762	Remote Similarity	NPD5519	Discontinued
0.6762	Remote Similarity	NPD6974	Phase 3
0.676	Remote Similarity	NPD6962	Phase 2
0.676	Remote Similarity	NPD1505	Phase 2
0.6752	Remote Similarity	NPD6219	Discontinued
0.6751	Remote Similarity	NPD7010	Phase 3
0.6743	Remote Similarity	NPD5532	Phase 2
0.6738	Remote Similarity	NPD4420	Approved
0.6736	Remote Similarity	NPD3257	Approved
0.6735	Remote Similarity	NPD7180	Phase 3
0.6734	Remote Similarity	NPD5640	Discontinued
0.673	Remote Similarity	NPD8461	Discontinued
0.6721	Remote Similarity	NPD5632	Approved
0.6718	Remote Similarity	NPD4558	Phase 2
0.6708	Remote Similarity	NPD8149	Discontinued
0.6707	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4923	Phase 1
0.6707	Remote Similarity	NPD7994	Phase 2
0.6707	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8016	Phase 3
0.6706	Remote Similarity	NPD6625	Approved
0.6706	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7558	Phase 2
0.6706	Remote Similarity	NPD6723	Discontinued
0.6695	Remote Similarity	NPD7467	Discontinued
0.6694	Remote Similarity	NPD3925	Approved
0.669	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5530	Phase 1
0.668	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7555	Discontinued
0.668	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6569	Phase 2
0.6667	Remote Similarity	NPD5850	Phase 3
0.6667	Remote Similarity	NPD5930	Phase 3
0.6654	Remote Similarity	NPD4876	Phase 3
0.6654	Remote Similarity	NPD4875	Phase 3
0.6654	Remote Similarity	NPD7853	Phase 2
0.6654	Remote Similarity	NPD7924	Phase 2
0.6654	Remote Similarity	NPD7925	Phase 2
0.6653	Remote Similarity	NPD7567	Approved
0.6653	Remote Similarity	NPD7225	Discontinued
0.6653	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7222	Phase 2
0.6652	Remote Similarity	NPD6281	Approved
0.6642	Remote Similarity	NPD7689	Approved
0.6641	Remote Similarity	NPD8100	Phase 3
0.6639	Remote Similarity	NPD4037	Approved
0.6639	Remote Similarity	NPD4039	Approved
0.6639	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4035	Approved
0.6639	Remote Similarity	NPD32	Approved
0.6639	Remote Similarity	NPD4122	Approved
0.6639	Remote Similarity	NPD4036	Approved
0.6639	Remote Similarity	NPD4034	Approved
0.6639	Remote Similarity	NPD4038	Approved
0.6639	Remote Similarity	NPD31	Approved
0.6639	Remote Similarity	NPD4033	Approved
0.6632	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3258	Approved
0.6626	Remote Similarity	NPD2899	Discontinued
0.6623	Remote Similarity	NPD2334	Discontinued
0.6622	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5601	Phase 2
0.661	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7233	Approved
0.6609	Remote Similarity	NPD7234	Approved
0.6602	Remote Similarity	NPD6825	Phase 1
0.66	Remote Similarity	NPD7223	Discontinued
0.66	Remote Similarity	NPD7224	Discontinued
0.6598	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6550	Discontinued
0.6581	Remote Similarity	NPD5512	Phase 3
0.6574	Remote Similarity	NPD4328	Approved
0.6574	Remote Similarity	NPD4845	Discontinued
0.6573	Remote Similarity	NPD6298	Discontinued
0.6571	Remote Similarity	NPD5612	Discontinued
0.6571	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD1038	Approved
0.6567	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4551	Phase 2
0.6565	Remote Similarity	NPD8101	Phase 3
0.6556	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6975	Discontinued
0.6553	Remote Similarity	NPD8463	Approved
0.6552	Remote Similarity	NPD8358	Approved
0.6552	Remote Similarity	NPD6276	Discontinued
0.6552	Remote Similarity	NPD3328	Phase 2
0.6549	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD2060	Approved
0.6537	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5070	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