NPASS Compound

Structure

NPC472409 OpenBabel07101718182D 23 26 0 0 1 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 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 6.0622 -1.5000 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 5.1962 -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 0.8660 1.5000 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 0.8660 -1.5000 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 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 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 3 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 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.13
Volume:	325.529
LogP:	4.816
LogD:	4.426
LogS:	-4.897
# Rotatable Bonds:	1
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	3.099
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.63
MDCK Permeability:	1.383969902235549e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	98.7154769897461%
Volume Distribution (VD):	0.595
Pgp-substrate:	1.0333749055862427%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.578
CYP2C19-inhibitor:	0.962
CYP2C19-substrate:	0.454
CYP2C9-inhibitor:	0.942
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.589
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	3.451
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.872
Drug-inuced Liver Injury (DILI):	0.651
AMES Toxicity:	0.351
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.696
Skin Sensitization:	0.166
Carcinogencity:	0.791
Eye Corrosion:	0.003
Eye Irritation:	0.086
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC472409

Natural Product ID:	NPC472409
*Common Name:**	(-)-Isolonchocarpin
IUPAC Name:	8,8-dimethyl-2-phenyl-2,3-dihydropyrano[2,3-f]chromen-4-one
Synonyms:
Standard InCHIKey:	GJRSGESHUAFWMY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O3/c1-20(2)11-10-15-17(23-20)9-8-14-16(21)12-18(22-19(14)15)13-6-4-3-5-7-13/h3-11,18H,12H2,1-2H3
SMILES:	O=C1CC(Oc2c1ccc1c2C=CC(O1)(C)C)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401061
PubChem CID:	12311091
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
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25630222]
NPO19856	Millettia pulchra	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	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	1.54	n.a.	PMID[496353]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	114.0	%	PMID[496353]

☑ 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 NPC472409 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	438
0.1-0.2	1688
0.2-0.3	4344
0.3-0.4	11587
0.4-0.5	6633
0.5-0.6	4180
0.6-0.7	6296
0.7-0.8	5076
0.8-0.85	1462
0.85-0.9	744
0.9-0.95	237
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9781	High Similarity	NPC59522
0.9778	High Similarity	NPC11566
0.9635	High Similarity	NPC52576
0.963	High Similarity	NPC259685
0.963	High Similarity	NPC157855
0.9571	High Similarity	NPC23728
0.9571	High Similarity	NPC110303
0.9565	High Similarity	NPC147145
0.9559	High Similarity	NPC17848
0.9556	High Similarity	NPC161196
0.9504	High Similarity	NPC132592
0.9504	High Similarity	NPC160821
0.95	High Similarity	NPC475052
0.95	High Similarity	NPC195621
0.95	High Similarity	NPC176229
0.95	High Similarity	NPC83357
0.95	High Similarity	NPC301276
0.95	High Similarity	NPC214774
0.95	High Similarity	NPC54577
0.95	High Similarity	NPC312973
0.95	High Similarity	NPC267375
0.95	High Similarity	NPC246948
0.95	High Similarity	NPC470647
0.95	High Similarity	NPC111786
0.95	High Similarity	NPC20488
0.95	High Similarity	NPC88964
0.95	High Similarity	NPC67805
0.95	High Similarity	NPC142405
0.9481	High Similarity	NPC99854
0.9433	High Similarity	NPC473077
0.9433	High Similarity	NPC296998
0.9433	High Similarity	NPC283234
0.9429	High Similarity	NPC209040
0.9429	High Similarity	NPC179970
0.9412	High Similarity	NPC254741
0.9407	High Similarity	NPC125269
0.9403	High Similarity	NPC229646
0.9366	High Similarity	NPC161191
0.9357	High Similarity	NPC169591
0.9357	High Similarity	NPC91560
0.9357	High Similarity	NPC39329
0.9357	High Similarity	NPC149026
0.9357	High Similarity	NPC257097
0.9357	High Similarity	NPC310130
0.9357	High Similarity	NPC150408
0.9357	High Similarity	NPC316816
0.9357	High Similarity	NPC68104
0.9357	High Similarity	NPC214166
0.9357	High Similarity	NPC143896
0.9357	High Similarity	NPC478086
0.9357	High Similarity	NPC38219
0.9357	High Similarity	NPC75049
0.9357	High Similarity	NPC221432
0.9357	High Similarity	NPC164980
0.9357	High Similarity	NPC175504
0.9353	High Similarity	NPC103362
0.9353	High Similarity	NPC22467
0.9338	High Similarity	NPC46869
0.9333	High Similarity	NPC292998
0.9328	High Similarity	NPC284424
0.9301	High Similarity	NPC164299
0.9296	High Similarity	NPC282335
0.9296	High Similarity	NPC79469
0.9296	High Similarity	NPC97716
0.9296	High Similarity	NPC471285
0.9296	High Similarity	NPC201731
0.9296	High Similarity	NPC24673
0.9296	High Similarity	NPC104406
0.9296	High Similarity	NPC218300
0.9296	High Similarity	NPC237635
0.9291	High Similarity	NPC319752
0.9291	High Similarity	NPC473013
0.9291	High Similarity	NPC236766
0.9291	High Similarity	NPC197252
0.9291	High Similarity	NPC131579
0.9291	High Similarity	NPC131568
0.9291	High Similarity	NPC473015
0.9286	High Similarity	NPC228504
0.9286	High Similarity	NPC161506
0.9286	High Similarity	NPC306829
0.9286	High Similarity	NPC227579
0.9286	High Similarity	NPC324134
0.9286	High Similarity	NPC78
0.9286	High Similarity	NPC66515
0.9286	High Similarity	NPC166482
0.9286	High Similarity	NPC194432
0.9286	High Similarity	NPC265040
0.9286	High Similarity	NPC32739
0.9286	High Similarity	NPC220998
0.9286	High Similarity	NPC177354
0.9286	High Similarity	NPC125855
0.9286	High Similarity	NPC182852
0.9286	High Similarity	NPC107572
0.9286	High Similarity	NPC76372
0.9286	High Similarity	NPC148757
0.9286	High Similarity	NPC11561
0.9286	High Similarity	NPC166934
0.9286	High Similarity	NPC328164
0.9286	High Similarity	NPC10937
0.9286	High Similarity	NPC64915
0.9286	High Similarity	NPC167624
0.9286	High Similarity	NPC226636
0.9286	High Similarity	NPC37496
0.9286	High Similarity	NPC324436
0.9286	High Similarity	NPC223500
0.9286	High Similarity	NPC40833
0.9286	High Similarity	NPC1089
0.9286	High Similarity	NPC76338
0.9286	High Similarity	NPC296917
0.9281	High Similarity	NPC150522
0.9281	High Similarity	NPC305355
0.9281	High Similarity	NPC475680
0.9259	High Similarity	NPC473655
0.9259	High Similarity	NPC101294
0.9241	High Similarity	NPC40033
0.9236	High Similarity	NPC472633
0.9231	High Similarity	NPC6511
0.9231	High Similarity	NPC266572
0.9231	High Similarity	NPC189087
0.9231	High Similarity	NPC321623
0.9225	High Similarity	NPC470134
0.9225	High Similarity	NPC470131
0.9225	High Similarity	NPC127059
0.9225	High Similarity	NPC476088
0.9225	High Similarity	NPC470132
0.9225	High Similarity	NPC285630
0.9225	High Similarity	NPC109183
0.9225	High Similarity	NPC474161
0.9225	High Similarity	NPC470133
0.9225	High Similarity	NPC473078
0.922	High Similarity	NPC81697
0.922	High Similarity	NPC18585
0.922	High Similarity	NPC278249
0.922	High Similarity	NPC166138
0.922	High Similarity	NPC125894
0.922	High Similarity	NPC219915
0.922	High Similarity	NPC107177
0.922	High Similarity	NPC223812
0.922	High Similarity	NPC106985
0.922	High Similarity	NPC17262
0.922	High Similarity	NPC85162
0.922	High Similarity	NPC77794
0.922	High Similarity	NPC185276
0.9214	High Similarity	NPC64908
0.9214	High Similarity	NPC156190
0.9214	High Similarity	NPC147688
0.9214	High Similarity	NPC324386
0.9214	High Similarity	NPC17170
0.9214	High Similarity	NPC96408
0.9214	High Similarity	NPC110969
0.9214	High Similarity	NPC213322
0.9214	High Similarity	NPC248372
0.9214	High Similarity	NPC205006
0.9214	High Similarity	NPC156590
0.9214	High Similarity	NPC118840
0.9214	High Similarity	NPC166689
0.9214	High Similarity	NPC312391
0.9214	High Similarity	NPC279650
0.9214	High Similarity	NPC3188
0.9214	High Similarity	NPC4743
0.9214	High Similarity	NPC110038
0.9214	High Similarity	NPC258630
0.9191	High Similarity	NPC223354
0.9185	High Similarity	NPC278556
0.9179	High Similarity	NPC228184
0.9178	High Similarity	NPC7989
0.9178	High Similarity	NPC472583
0.9178	High Similarity	NPC223701
0.9167	High Similarity	NPC5173
0.9167	High Similarity	NPC473016
0.9167	High Similarity	NPC104236
0.9167	High Similarity	NPC164205
0.9161	High Similarity	NPC472627
0.9155	High Similarity	NPC470136
0.9155	High Similarity	NPC87486
0.9155	High Similarity	NPC470135
0.9155	High Similarity	NPC39045
0.9155	High Similarity	NPC311741
0.9155	High Similarity	NPC124780
0.9155	High Similarity	NPC235217
0.9155	High Similarity	NPC171656
0.9155	High Similarity	NPC473014
0.9155	High Similarity	NPC234629
0.9149	High Similarity	NPC217083
0.9149	High Similarity	NPC214236
0.9149	High Similarity	NPC299080
0.9149	High Similarity	NPC78803
0.9149	High Similarity	NPC59739
0.9149	High Similarity	NPC144499
0.9149	High Similarity	NPC62840
0.9149	High Similarity	NPC293852
0.9143	High Similarity	NPC172986
0.9143	High Similarity	NPC159275
0.9143	High Similarity	NPC261227
0.9143	High Similarity	NPC171094
0.9143	High Similarity	NPC235239
0.9143	High Similarity	NPC188243
0.9143	High Similarity	NPC270883
0.9143	High Similarity	NPC6407
0.9143	High Similarity	NPC69769

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 NPC472409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	995
0.2-0.3	1490
0.3-0.4	2720
0.4-0.5	1850
0.5-0.6	1139
0.6-0.7	408
0.7-0.8	130
0.8-0.85	19
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9556	High Similarity	NPD2796	Approved
0.9021	High Similarity	NPD7410	Clinical (unspecified phase)
0.9	High Similarity	NPD1549	Phase 2
0.8929	High Similarity	NPD1552	Clinical (unspecified phase)
0.8929	High Similarity	NPD1550	Clinical (unspecified phase)
0.8912	High Similarity	NPD7411	Suspended
0.8889	High Similarity	NPD4378	Clinical (unspecified phase)
0.8844	High Similarity	NPD4380	Phase 2
0.8792	High Similarity	NPD7096	Clinical (unspecified phase)
0.8733	High Similarity	NPD8443	Clinical (unspecified phase)
0.8725	High Similarity	NPD6801	Discontinued
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD7819	Suspended
0.8652	High Similarity	NPD1510	Phase 2
0.8633	High Similarity	NPD1240	Approved
0.8627	High Similarity	NPD5494	Approved
0.8618	High Similarity	NPD7075	Discontinued
0.8562	High Similarity	NPD6799	Approved
0.8542	High Similarity	NPD1243	Approved
0.8511	High Similarity	NPD1607	Approved
0.8507	High Similarity	NPD1547	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD3748	Approved
0.8389	Intermediate Similarity	NPD920	Approved
0.8378	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8291	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD5403	Approved
0.8255	Intermediate Similarity	NPD5401	Approved
0.825	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8194	Intermediate Similarity	NPD7768	Phase 2
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8108	Intermediate Similarity	NPD3750	Approved
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD6832	Phase 2
0.8067	Intermediate Similarity	NPD1511	Approved
0.8065	Intermediate Similarity	NPD2801	Approved
0.8063	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6166	Phase 2
0.8063	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD919	Approved
0.7962	Intermediate Similarity	NPD3882	Suspended
0.7961	Intermediate Similarity	NPD1512	Approved
0.7914	Intermediate Similarity	NPD7054	Approved
0.7898	Intermediate Similarity	NPD5402	Approved
0.7891	Intermediate Similarity	NPD2799	Discontinued
0.7875	Intermediate Similarity	NPD1247	Approved
0.7866	Intermediate Similarity	NPD7472	Approved
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7853	Intermediate Similarity	NPD3818	Discontinued
0.7848	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD2313	Discontinued
0.7838	Intermediate Similarity	NPD1551	Phase 2
0.7821	Intermediate Similarity	NPD5890	Approved
0.7821	Intermediate Similarity	NPD5889	Approved
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.7817	Intermediate Similarity	NPD2798	Approved
0.7808	Intermediate Similarity	NPD5124	Phase 1
0.7808	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.78	Intermediate Similarity	NPD2800	Approved
0.7786	Intermediate Similarity	NPD3972	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.777	Intermediate Similarity	NPD7033	Discontinued
0.7756	Intermediate Similarity	NPD6585	Discontinued
0.7755	Intermediate Similarity	NPD6651	Approved
0.7733	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7724	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2935	Discontinued
0.7711	Intermediate Similarity	NPD5953	Discontinued
0.7704	Intermediate Similarity	NPD1241	Discontinued
0.7697	Intermediate Similarity	NPD7286	Phase 2
0.7687	Intermediate Similarity	NPD1933	Approved
0.7682	Intermediate Similarity	NPD2654	Approved
0.7669	Intermediate Similarity	NPD3926	Phase 2
0.7667	Intermediate Similarity	NPD2344	Approved
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7632	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3266	Approved
0.7622	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3267	Approved
0.7619	Intermediate Similarity	NPD4307	Phase 2
0.7619	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6100	Approved
0.76	Intermediate Similarity	NPD6099	Approved
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD4908	Phase 1
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.7582	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1548	Phase 1
0.755	Intermediate Similarity	NPD2346	Discontinued
0.7548	Intermediate Similarity	NPD2534	Approved
0.7548	Intermediate Similarity	NPD2532	Approved
0.7548	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD3142	Approved
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD3140	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD3268	Approved
0.747	Intermediate Similarity	NPD7473	Discontinued
0.7468	Intermediate Similarity	NPD2309	Approved
0.7468	Intermediate Similarity	NPD3887	Approved
0.7468	Intermediate Similarity	NPD3226	Approved
0.7465	Intermediate Similarity	NPD1610	Phase 2
0.7448	Intermediate Similarity	NPD1019	Discontinued
0.7425	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4308	Phase 3
0.7417	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD9717	Approved
0.7403	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4288	Approved
0.7343	Intermediate Similarity	NPD422	Phase 1
0.7337	Intermediate Similarity	NPD1729	Discontinued
0.7329	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD6279	Approved
0.7329	Intermediate Similarity	NPD6280	Approved
0.7325	Intermediate Similarity	NPD4662	Approved
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4661	Approved
0.7324	Intermediate Similarity	NPD17	Approved
0.7322	Intermediate Similarity	NPD7584	Approved
0.732	Intermediate Similarity	NPD1471	Phase 3
0.731	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD1876	Approved
0.7297	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD943	Approved
0.7261	Intermediate Similarity	NPD7390	Discontinued
0.7251	Intermediate Similarity	NPD6104	Discontinued
0.725	Intermediate Similarity	NPD7458	Discontinued
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7247	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4361	Phase 2
0.7222	Intermediate Similarity	NPD7577	Discontinued
0.7219	Intermediate Similarity	NPD3751	Discontinued
0.7208	Intermediate Similarity	NPD2353	Approved
0.7208	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2403	Approved
0.7186	Intermediate Similarity	NPD6808	Phase 2
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7183	Intermediate Similarity	NPD9545	Approved
0.7179	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD1465	Phase 2
0.7172	Intermediate Similarity	NPD1608	Approved
0.717	Intermediate Similarity	NPD6273	Approved
0.7161	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1651	Approved
0.7118	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1652	Phase 2
0.7114	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD5711	Approved
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.707	Intermediate Similarity	NPD7466	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7069	Intermediate Similarity	NPD8312	Approved
0.7063	Intermediate Similarity	NPD5049	Phase 3
0.7062	Intermediate Similarity	NPD4287	Approved
0.7044	Intermediate Similarity	NPD7213	Phase 3
0.7044	Intermediate Similarity	NPD7212	Phase 2
0.7042	Intermediate Similarity	NPD9493	Approved
0.7039	Intermediate Similarity	NPD1613	Approved
0.7039	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8285	Discontinued
0.7032	Intermediate Similarity	NPD4476	Approved
0.7032	Intermediate Similarity	NPD4477	Approved
0.7025	Intermediate Similarity	NPD2354	Approved
0.702	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4749	Approved
0.7	Intermediate Similarity	NPD5535	Approved
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6994	Remote Similarity	NPD3823	Discontinued

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