NPASS Compound

Structure

CID59522 OpenBabel06191715392D 29 33 0 0 1 0 0 0 0 0999 V2000 -8.0530 -3.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5876 -1.8912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 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 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 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 -6.9282 -1.0000 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 -4.3301 0.5000 0.0000 C 0 0 1 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 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 26 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 15 1 6 0 0 0 22 27 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.17
Volume:	409.607
LogP:	6.416
LogD:	5.183
LogS:	-4.284
# Rotatable Bonds:	1
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.623
Synthetic Accessibility Score:	3.666
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.678
MDCK Permeability:	1.4477057447948027e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.475
30% Bioavailability (F30%):	0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	100.15230560302734%
Volume Distribution (VD):	0.571
Pgp-substrate:	1.4828722476959229%

ADMET: Metabolism

CYP1A2-inhibitor:	0.596
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.451
CYP2C9-inhibitor:	0.95
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.957
CYP2D6-substrate:	0.699
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.524

ADMET: Excretion

Clearance (CL):	3.95
Half-life (T1/2):	0.07

ADMET: Toxicity

hERG Blockers:	0.828
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.332
Skin Sensitization:	0.085
Carcinogencity:	0.932
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC59522

Natural Product ID:	NPC59522
*Common Name:**	Xambioona
IUPAC Name:	(2S)-2-(2,2-dimethylchromen-6-yl)-8,8-dimethyl-2,3-dihydropyrano[2,3-f]chromen-4-one
Synonyms:
Standard InCHIKey:	FGJUXFVUOCKRCY-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C25H24O4/c1-24(2)11-9-16-13-15(5-7-20(16)28-24)22-14-19(26)17-6-8-21-18(23(17)27-22)10-12-25(3,4)29-21/h5-13,22H,14H2,1-4H3/t22-/m0/s1
SMILES:	O=C1C[C@H](Oc2c1ccc1c2C=CC(O1)(C)C)c1ccc2c(c1)C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2437375
PubChem CID:	73352581
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	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
Others	10

Activity Type	# Activity
Cell Line	5
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	50.0	%	PMID[504780]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	76.9	%	PMID[504781]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.8	n.a.	PMID[504781]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	6.9	%	PMID[504781]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	0.0	%	PMID[504781]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	10.9	%	PMID[504781]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	0.0	%	PMID[504781]
NPT660	Cell Line	SW480	Homo sapiens	Inhibition	=	7.9	%	PMID[504781]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	0.0	%	PMID[504781]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[504781]

☑ 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 NPC59522 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	440
0.1-0.2	1623
0.2-0.3	4216
0.3-0.4	10761
0.4-0.5	7542
0.5-0.6	3951
0.6-0.7	6236
0.7-0.8	5127
0.8-0.85	1630
0.85-0.9	855
0.9-0.95	304
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9854	High Similarity	NPC52576
0.9781	High Similarity	NPC472409
0.9708	High Similarity	NPC11566
0.9643	High Similarity	NPC179970
0.9635	High Similarity	NPC17848
0.9577	High Similarity	NPC161191
0.9562	High Similarity	NPC157855
0.9562	High Similarity	NPC259685
0.9507	High Similarity	NPC218300
0.9507	High Similarity	NPC282335
0.9507	High Similarity	NPC23728
0.9507	High Similarity	NPC110303
0.95	High Similarity	NPC147145
0.9489	High Similarity	NPC161196
0.9441	High Similarity	NPC160821
0.9441	High Similarity	NPC189087
0.9441	High Similarity	NPC321623
0.9441	High Similarity	NPC132592
0.9437	High Similarity	NPC214774
0.9437	High Similarity	NPC176229
0.9437	High Similarity	NPC111786
0.9437	High Similarity	NPC67805
0.9437	High Similarity	NPC301276
0.9437	High Similarity	NPC312973
0.9437	High Similarity	NPC195621
0.9437	High Similarity	NPC88964
0.9437	High Similarity	NPC475052
0.9437	High Similarity	NPC470647
0.9437	High Similarity	NPC54577
0.9437	High Similarity	NPC246948
0.9437	High Similarity	NPC83357
0.9437	High Similarity	NPC142405
0.9437	High Similarity	NPC267375
0.9437	High Similarity	NPC20488
0.9416	High Similarity	NPC99854
0.9416	High Similarity	NPC46869
0.9371	High Similarity	NPC237635
0.9371	High Similarity	NPC296998
0.9371	High Similarity	NPC473077
0.9371	High Similarity	NPC79469
0.9371	High Similarity	NPC24673
0.9371	High Similarity	NPC201731
0.9371	High Similarity	NPC97716
0.9371	High Similarity	NPC104406
0.9371	High Similarity	NPC283234
0.9366	High Similarity	NPC319752
0.9366	High Similarity	NPC209040
0.9348	High Similarity	NPC254741
0.9343	High Similarity	NPC125269
0.932	High Similarity	NPC477530
0.9306	High Similarity	NPC6511
0.9306	High Similarity	NPC266572
0.9301	High Similarity	NPC476088
0.9301	High Similarity	NPC474161
0.9296	High Similarity	NPC150408
0.9296	High Similarity	NPC143896
0.9296	High Similarity	NPC310130
0.9296	High Similarity	NPC39329
0.9296	High Similarity	NPC221432
0.9296	High Similarity	NPC68104
0.9296	High Similarity	NPC91560
0.9296	High Similarity	NPC75049
0.9296	High Similarity	NPC164980
0.9296	High Similarity	NPC478086
0.9296	High Similarity	NPC149026
0.9296	High Similarity	NPC214166
0.9296	High Similarity	NPC257097
0.9296	High Similarity	NPC169591
0.9296	High Similarity	NPC38219
0.9296	High Similarity	NPC316816
0.9296	High Similarity	NPC175504
0.9291	High Similarity	NPC103362
0.9291	High Similarity	NPC22467
0.9241	High Similarity	NPC5173
0.9241	High Similarity	NPC164299
0.9236	High Similarity	NPC471285
0.9231	High Similarity	NPC473013
0.9231	High Similarity	NPC131568
0.9231	High Similarity	NPC131579
0.9231	High Similarity	NPC236766
0.9231	High Similarity	NPC473015
0.9231	High Similarity	NPC197252
0.9225	High Similarity	NPC194432
0.9225	High Similarity	NPC125855
0.9225	High Similarity	NPC296917
0.9225	High Similarity	NPC76372
0.9225	High Similarity	NPC66515
0.9225	High Similarity	NPC161506
0.9225	High Similarity	NPC228504
0.9225	High Similarity	NPC148757
0.9225	High Similarity	NPC59739
0.9225	High Similarity	NPC293852
0.9225	High Similarity	NPC78
0.9225	High Similarity	NPC166482
0.9225	High Similarity	NPC10937
0.9225	High Similarity	NPC220998
0.9225	High Similarity	NPC177354
0.9225	High Similarity	NPC182852
0.9225	High Similarity	NPC64915
0.9225	High Similarity	NPC167624
0.9225	High Similarity	NPC107572
0.9225	High Similarity	NPC299080
0.9225	High Similarity	NPC226636
0.9225	High Similarity	NPC11561
0.9225	High Similarity	NPC166934
0.9225	High Similarity	NPC223500
0.9225	High Similarity	NPC1089
0.9225	High Similarity	NPC217083
0.9225	High Similarity	NPC214236
0.9225	High Similarity	NPC78803
0.9225	High Similarity	NPC37496
0.9225	High Similarity	NPC32739
0.9225	High Similarity	NPC40833
0.9225	High Similarity	NPC324436
0.9225	High Similarity	NPC227579
0.9225	High Similarity	NPC62840
0.9225	High Similarity	NPC328164
0.9225	High Similarity	NPC265040
0.9225	High Similarity	NPC76338
0.9225	High Similarity	NPC324134
0.9225	High Similarity	NPC306829
0.922	High Similarity	NPC150522
0.9197	High Similarity	NPC473655
0.9197	High Similarity	NPC101294
0.9197	High Similarity	NPC229646
0.9184	High Similarity	NPC40033
0.9178	High Similarity	NPC5840
0.9178	High Similarity	NPC472633
0.9178	High Similarity	NPC189270
0.9178	High Similarity	NPC188403
0.9167	High Similarity	NPC470131
0.9167	High Similarity	NPC470134
0.9167	High Similarity	NPC473078
0.9167	High Similarity	NPC470132
0.9167	High Similarity	NPC109183
0.9167	High Similarity	NPC285630
0.9167	High Similarity	NPC127059
0.9167	High Similarity	NPC470133
0.9161	High Similarity	NPC166138
0.9161	High Similarity	NPC107177
0.9161	High Similarity	NPC18585
0.9161	High Similarity	NPC85162
0.9161	High Similarity	NPC77794
0.9161	High Similarity	NPC278249
0.9161	High Similarity	NPC106985
0.9161	High Similarity	NPC185276
0.9161	High Similarity	NPC81697
0.9161	High Similarity	NPC125894
0.9161	High Similarity	NPC223812
0.9161	High Similarity	NPC219915
0.9155	High Similarity	NPC279650
0.9155	High Similarity	NPC147688
0.9155	High Similarity	NPC201820
0.9155	High Similarity	NPC17170
0.9155	High Similarity	NPC248372
0.9155	High Similarity	NPC64908
0.9155	High Similarity	NPC166689
0.9155	High Similarity	NPC110038
0.9155	High Similarity	NPC156590
0.9155	High Similarity	NPC4743
0.9155	High Similarity	NPC96408
0.9155	High Similarity	NPC118840
0.9155	High Similarity	NPC3188
0.9155	High Similarity	NPC324386
0.9155	High Similarity	NPC213322
0.9155	High Similarity	NPC205006
0.9155	High Similarity	NPC258630
0.9155	High Similarity	NPC110969
0.9155	High Similarity	NPC312391
0.9155	High Similarity	NPC156190
0.913	High Similarity	NPC292998
0.913	High Similarity	NPC223354
0.9124	High Similarity	NPC278556
0.9124	High Similarity	NPC284424
0.9122	High Similarity	NPC223701
0.9122	High Similarity	NPC7989
0.9122	High Similarity	NPC88983
0.9122	High Similarity	NPC472583
0.911	High Similarity	NPC104236
0.911	High Similarity	NPC164205
0.911	High Similarity	NPC473016
0.911	High Similarity	NPC3642
0.9103	High Similarity	NPC472627
0.9097	High Similarity	NPC470135
0.9097	High Similarity	NPC473014
0.9097	High Similarity	NPC470136
0.9097	High Similarity	NPC124780
0.9097	High Similarity	NPC39045
0.9097	High Similarity	NPC234629
0.9097	High Similarity	NPC87486
0.9097	High Similarity	NPC235217
0.9097	High Similarity	NPC171656
0.9097	High Similarity	NPC311741
0.9091	High Similarity	NPC144499
0.9085	High Similarity	NPC172986
0.9085	High Similarity	NPC235239
0.9085	High Similarity	NPC110228
0.9085	High Similarity	NPC171094
0.9085	High Similarity	NPC159275
0.9085	High Similarity	NPC188243

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 NPC59522 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	986
0.2-0.3	1519
0.3-0.4	2651
0.4-0.5	1880
0.5-0.6	1139
0.6-0.7	417
0.7-0.8	143
0.8-0.85	23
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9348	High Similarity	NPD2796	Approved
0.8966	High Similarity	NPD7410	Clinical (unspecified phase)
0.8944	High Similarity	NPD1549	Phase 2
0.8873	High Similarity	NPD1552	Clinical (unspecified phase)
0.8873	High Similarity	NPD1550	Clinical (unspecified phase)
0.8859	High Similarity	NPD7411	Suspended
0.8836	High Similarity	NPD4378	Clinical (unspecified phase)
0.8792	High Similarity	NPD4380	Phase 2
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.8684	High Similarity	NPD8443	Clinical (unspecified phase)
0.8675	High Similarity	NPD6801	Discontinued
0.8618	High Similarity	NPD2393	Clinical (unspecified phase)
0.8618	High Similarity	NPD7819	Suspended
0.8601	High Similarity	NPD1510	Phase 2
0.8581	High Similarity	NPD5494	Approved
0.8571	High Similarity	NPD7075	Discontinued
0.8514	High Similarity	NPD6799	Approved
0.8452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1240	Approved
0.8367	Intermediate Similarity	NPD1243	Approved
0.8365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD3748	Approved
0.8344	Intermediate Similarity	NPD920	Approved
0.8344	Intermediate Similarity	NPD5403	Approved
0.8333	Intermediate Similarity	NPD5401	Approved
0.8333	Intermediate Similarity	NPD1607	Approved
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1934	Approved
0.8301	Intermediate Similarity	NPD6599	Discontinued
0.8291	Intermediate Similarity	NPD6959	Discontinued
0.8243	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7768	Phase 2
0.8137	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6166	Phase 2
0.8089	Intermediate Similarity	NPD3817	Phase 2
0.8067	Intermediate Similarity	NPD3750	Approved
0.8056	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD6832	Phase 2
0.8026	Intermediate Similarity	NPD1511	Approved
0.8025	Intermediate Similarity	NPD2801	Approved
0.7988	Intermediate Similarity	NPD7054	Approved
0.7987	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD5402	Approved
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7939	Intermediate Similarity	NPD7472	Approved
0.7937	Intermediate Similarity	NPD919	Approved
0.7925	Intermediate Similarity	NPD3882	Suspended
0.7922	Intermediate Similarity	NPD1512	Approved
0.7892	Intermediate Similarity	NPD6797	Phase 2
0.7891	Intermediate Similarity	NPD5124	Phase 1
0.7891	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2799	Discontinued
0.7844	Intermediate Similarity	NPD7251	Discontinued
0.784	Intermediate Similarity	NPD1247	Approved
0.7818	Intermediate Similarity	NPD3818	Discontinued
0.7812	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD2313	Discontinued
0.78	Intermediate Similarity	NPD1551	Phase 2
0.7798	Intermediate Similarity	NPD7808	Phase 3
0.7785	Intermediate Similarity	NPD5889	Approved
0.7785	Intermediate Similarity	NPD5890	Approved
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7763	Intermediate Similarity	NPD2800	Approved
0.7738	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD7033	Discontinued
0.7722	Intermediate Similarity	NPD6585	Discontinued
0.7718	Intermediate Similarity	NPD6651	Approved
0.7697	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD5953	Discontinued
0.7665	Intermediate Similarity	NPD7286	Phase 2
0.7655	Intermediate Similarity	NPD2798	Approved
0.7651	Intermediate Similarity	NPD1933	Approved
0.7647	Intermediate Similarity	NPD2654	Approved
0.7636	Intermediate Similarity	NPD3926	Phase 2
0.7622	Intermediate Similarity	NPD3972	Approved
0.7597	Intermediate Similarity	NPD4628	Phase 3
0.7597	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3266	Approved
0.7586	Intermediate Similarity	NPD3267	Approved
0.7584	Intermediate Similarity	NPD4307	Phase 2
0.7557	Intermediate Similarity	NPD4363	Phase 3
0.7557	Intermediate Similarity	NPD4360	Phase 2
0.7551	Intermediate Similarity	NPD4908	Phase 1
0.7536	Intermediate Similarity	NPD1241	Discontinued
0.7533	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7516	Intermediate Similarity	NPD2534	Approved
0.7516	Intermediate Similarity	NPD2533	Approved
0.7472	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6232	Discontinued
0.7466	Intermediate Similarity	NPD1203	Approved
0.7453	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6100	Approved
0.7451	Intermediate Similarity	NPD6099	Approved
0.745	Intermediate Similarity	NPD1296	Phase 2
0.745	Intermediate Similarity	NPD3268	Approved
0.744	Intermediate Similarity	NPD7473	Discontinued
0.7438	Intermediate Similarity	NPD3226	Approved
0.7436	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3887	Approved
0.7415	Intermediate Similarity	NPD1019	Discontinued
0.7397	Intermediate Similarity	NPD3225	Approved
0.7396	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1548	Phase 1
0.7386	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7379	Intermediate Similarity	NPD9717	Approved
0.7372	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3142	Approved
0.7351	Intermediate Similarity	NPD3140	Approved
0.7347	Intermediate Similarity	NPD2797	Approved
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7390	Discontinued
0.7329	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7325	Intermediate Similarity	NPD2309	Approved
0.7317	Intermediate Similarity	NPD4288	Approved
0.731	Intermediate Similarity	NPD1610	Phase 2
0.7301	Intermediate Similarity	NPD6844	Discontinued
0.7297	Intermediate Similarity	NPD7584	Approved
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.729	Intermediate Similarity	NPD1471	Phase 3
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7237	Intermediate Similarity	NPD943	Approved
0.7225	Intermediate Similarity	NPD6104	Discontinued
0.7222	Intermediate Similarity	NPD4361	Phase 2
0.7222	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6798	Discontinued
0.7209	Intermediate Similarity	NPD1729	Discontinued
0.7195	Intermediate Similarity	NPD6280	Approved
0.7195	Intermediate Similarity	NPD6279	Approved
0.7192	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD4661	Approved
0.7188	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2353	Approved
0.7176	Intermediate Similarity	NPD2403	Approved
0.7172	Intermediate Similarity	NPD17	Approved
0.7162	Intermediate Similarity	NPD1876	Approved
0.716	Intermediate Similarity	NPD6808	Phase 2
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD8455	Phase 2
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD7212	Phase 2
0.7125	Intermediate Similarity	NPD7213	Phase 3
0.7104	Intermediate Similarity	NPD8285	Discontinued
0.7091	Intermediate Similarity	NPD7577	Discontinued
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7086	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6780	Approved
0.7065	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6778	Approved
0.7065	Intermediate Similarity	NPD6782	Approved
0.7065	Intermediate Similarity	NPD6781	Approved
0.7065	Intermediate Similarity	NPD6777	Approved
0.7065	Intermediate Similarity	NPD6776	Approved
0.7065	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD5711	Approved
0.7039	Intermediate Similarity	NPD4287	Approved
0.7037	Intermediate Similarity	NPD5049	Phase 3
0.7037	Intermediate Similarity	NPD6273	Approved
0.7034	Intermediate Similarity	NPD9545	Approved
0.7027	Intermediate Similarity	NPD1608	Approved
0.7013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD2354	Approved
0.6994	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7097	Phase 1
0.6986	Remote Similarity	NPD1651	Approved
0.6975	Remote Similarity	NPD7447	Phase 1
0.6972	Remote Similarity	NPD5535	Approved
0.6971	Remote Similarity	NPD3823	Discontinued
0.6968	Remote Similarity	NPD6355	Discontinued
0.6952	Remote Similarity	NPD7696	Phase 3
0.6952	Remote Similarity	NPD7698	Approved
0.6952	Remote Similarity	NPD7435	Discontinued
0.6952	Remote Similarity	NPD7697	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