NPASS Compound

Structure

CID317492 OpenBabel06191716142D 26 29 0 0 1 0 0 0 0 0999 V2000 2.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 0.5219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 -2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5241 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 0.0219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -2.9781 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 9 2 0 0 0 0 2 9 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 15 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 25 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.09
Volume:	349.264
LogP:	3.88
LogD:	2.794
LogS:	-3.881
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	3.558
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.813
MDCK Permeability:	9.160653462458868e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	96.73529815673828%
Volume Distribution (VD):	0.425
Pgp-substrate:	1.8789492845535278%

ADMET: Metabolism

CYP1A2-inhibitor:	0.857
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.624
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.728
CYP2D6-substrate:	0.752
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	6.649
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.923
Carcinogencity:	0.322
Eye Corrosion:	0.003
Eye Irritation:	0.883
Respiratory Toxicity:	0.427

Download Data

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

Natural Product: NPC317492

Natural Product ID:	NPC317492
*Common Name:**	(+/-)-7,2',4'-Trihydroxy-5''-Isopropenyl-4'',5''-Dihydrofurano[2'',3'':5,6]Isoflavone
IUPAC Name:	8-(2,4-dihydroxyphenyl)-4-hydroxy-2-prop-1-en-2-yl-2,3-dihydrofuro[2,3-f]chromen-9-one
Synonyms:
Standard InCHIKey:	HHQAAUSMOBNXFL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O6/c1-9(2)16-6-12-15(23)7-17-18(20(12)26-16)19(24)13(8-25-17)11-4-3-10(21)5-14(11)22/h3-5,7-8,16,21-23H,1,6H2,2H3
SMILES:	CC(=C)C1Cc2c(O1)c1c(cc2O)occ(c1=O)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689270
PubChem CID:	51041993
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21265557]
NPO21353	Crotalaria lachnophora	Species	Fabaceae	Eukaryota	whole plant	Dschang (west region of Cameroon)	2007-SEP	PMID[21265557]
NPO21353	Crotalaria lachnophora	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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.3	mm	PMID[564479]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	7.0	mm	PMID[564479]

☑ 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 NPC317492 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	394
0.1-0.2	1655
0.2-0.3	3795
0.3-0.4	9616
0.4-0.5	8933
0.5-0.6	3810
0.6-0.7	5555
0.7-0.8	4645
0.8-0.85	2163
0.85-0.9	1596
0.9-0.95	446
0.95-1	89

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC168085
0.9658	High Similarity	NPC327269
0.9658	High Similarity	NPC31627
0.9658	High Similarity	NPC476238
0.9655	High Similarity	NPC321896
0.9655	High Similarity	NPC476185
0.9589	High Similarity	NPC471675
0.958	High Similarity	NPC224714
0.958	High Similarity	NPC234629
0.958	High Similarity	NPC311741
0.9524	High Similarity	NPC473996
0.9524	High Similarity	NPC285623
0.9521	High Similarity	NPC472421
0.9521	High Similarity	NPC61258
0.9517	High Similarity	NPC266572
0.9517	High Similarity	NPC39195
0.9514	High Similarity	NPC472629
0.951	High Similarity	NPC39329
0.951	High Similarity	NPC257097
0.951	High Similarity	NPC143896
0.951	High Similarity	NPC150408
0.951	High Similarity	NPC68104
0.951	High Similarity	NPC169591
0.951	High Similarity	NPC51887
0.951	High Similarity	NPC175504
0.951	High Similarity	NPC149026
0.951	High Similarity	NPC221432
0.951	High Similarity	NPC117836
0.951	High Similarity	NPC476178
0.951	High Similarity	NPC475705
0.951	High Similarity	NPC91560
0.951	High Similarity	NPC310130
0.951	High Similarity	NPC75049
0.951	High Similarity	NPC164980
0.9507	High Similarity	NPC110969
0.9507	High Similarity	NPC469404
0.9507	High Similarity	NPC52789
0.9507	High Similarity	NPC55832
0.9507	High Similarity	NPC26051
0.9507	High Similarity	NPC268204
0.9459	High Similarity	NPC1477
0.9459	High Similarity	NPC213608
0.9456	High Similarity	NPC474772
0.9456	High Similarity	NPC474744
0.9456	High Similarity	NPC472423
0.9456	High Similarity	NPC472580
0.9456	High Similarity	NPC472636
0.9456	High Similarity	NPC290671
0.9452	High Similarity	NPC226644
0.9452	High Similarity	NPC37226
0.9452	High Similarity	NPC5173
0.9448	High Similarity	NPC23728
0.9448	High Similarity	NPC308200
0.9448	High Similarity	NPC104406
0.9448	High Similarity	NPC24673
0.9448	High Similarity	NPC110303
0.9448	High Similarity	NPC97716
0.9448	High Similarity	NPC473077
0.9448	High Similarity	NPC296998
0.9448	High Similarity	NPC237635
0.9448	High Similarity	NPC201731
0.9448	High Similarity	NPC79469
0.9444	High Similarity	NPC470890
0.9444	High Similarity	NPC236766
0.9444	High Similarity	NPC319752
0.9444	High Similarity	NPC197252
0.9444	High Similarity	NPC87486
0.9444	High Similarity	NPC273538
0.9444	High Similarity	NPC473013
0.9444	High Similarity	NPC209040
0.9444	High Similarity	NPC216538
0.9444	High Similarity	NPC473015
0.9444	High Similarity	NPC124780
0.9441	High Similarity	NPC66515
0.9441	High Similarity	NPC306829
0.9441	High Similarity	NPC32739
0.9441	High Similarity	NPC76372
0.9441	High Similarity	NPC226636
0.9441	High Similarity	NPC107572
0.9441	High Similarity	NPC324134
0.9441	High Similarity	NPC167624
0.9441	High Similarity	NPC296917
0.9441	High Similarity	NPC166934
0.9441	High Similarity	NPC324436
0.9441	High Similarity	NPC194432
0.9441	High Similarity	NPC11561
0.9441	High Similarity	NPC161506
0.9441	High Similarity	NPC37496
0.9441	High Similarity	NPC228504
0.9441	High Similarity	NPC227579
0.9441	High Similarity	NPC220998
0.9441	High Similarity	NPC76338
0.9441	High Similarity	NPC78
0.9441	High Similarity	NPC166482
0.9441	High Similarity	NPC223500
0.9441	High Similarity	NPC10937
0.9441	High Similarity	NPC265040
0.9441	High Similarity	NPC177354
0.9441	High Similarity	NPC40833
0.9441	High Similarity	NPC64915
0.9441	High Similarity	NPC328164
0.9441	High Similarity	NPC182852
0.9441	High Similarity	NPC1089
0.9441	High Similarity	NPC125855
0.9441	High Similarity	NPC148757
0.9437	High Similarity	NPC326109
0.9437	High Similarity	NPC215311
0.9437	High Similarity	NPC253822
0.9437	High Similarity	NPC172986
0.9437	High Similarity	NPC159275
0.9437	High Similarity	NPC48624
0.9437	High Similarity	NPC213659
0.9437	High Similarity	NPC261227
0.9437	High Similarity	NPC101366
0.9437	High Similarity	NPC259166
0.9437	High Similarity	NPC270883
0.9437	High Similarity	NPC241100
0.9437	High Similarity	NPC219917
0.9437	High Similarity	NPC144118
0.9437	High Similarity	NPC172250
0.9437	High Similarity	NPC204985
0.9437	High Similarity	NPC80962
0.94	High Similarity	NPC65504
0.9392	High Similarity	NPC5871
0.9392	High Similarity	NPC477957
0.9388	High Similarity	NPC472633
0.9388	High Similarity	NPC37348
0.9388	High Similarity	NPC471115
0.9388	High Similarity	NPC29777
0.9384	High Similarity	NPC160821
0.9384	High Similarity	NPC145467
0.9384	High Similarity	NPC6511
0.9384	High Similarity	NPC132592
0.9379	High Similarity	NPC312973
0.9379	High Similarity	NPC88964
0.9379	High Similarity	NPC470647
0.9379	High Similarity	NPC142405
0.9379	High Similarity	NPC178343
0.9379	High Similarity	NPC474161
0.9379	High Similarity	NPC111786
0.9379	High Similarity	NPC24136
0.9379	High Similarity	NPC54577
0.9379	High Similarity	NPC475052
0.9379	High Similarity	NPC267375
0.9379	High Similarity	NPC67805
0.9379	High Similarity	NPC83357
0.9379	High Similarity	NPC301276
0.9379	High Similarity	NPC476088
0.9379	High Similarity	NPC306488
0.9379	High Similarity	NPC290133
0.9379	High Similarity	NPC299011
0.9379	High Similarity	NPC187282
0.9379	High Similarity	NPC195621
0.9379	High Similarity	NPC5820
0.9379	High Similarity	NPC20488
0.9379	High Similarity	NPC124729
0.9379	High Similarity	NPC176229
0.9379	High Similarity	NPC214774
0.9379	High Similarity	NPC246948
0.9375	High Similarity	NPC212932
0.9375	High Similarity	NPC478086
0.9375	High Similarity	NPC85162
0.9375	High Similarity	NPC9117
0.9375	High Similarity	NPC278249
0.9375	High Similarity	NPC166138
0.9375	High Similarity	NPC107177
0.9375	High Similarity	NPC190637
0.9375	High Similarity	NPC24821
0.9375	High Similarity	NPC81697
0.9375	High Similarity	NPC185276
0.9375	High Similarity	NPC214166
0.9375	High Similarity	NPC18585
0.9375	High Similarity	NPC316816
0.9375	High Similarity	NPC125894
0.9375	High Similarity	NPC223812
0.9375	High Similarity	NPC293053
0.9375	High Similarity	NPC77794
0.9375	High Similarity	NPC106985
0.9371	High Similarity	NPC96408
0.9371	High Similarity	NPC248372
0.9371	High Similarity	NPC4743
0.9371	High Similarity	NPC147688
0.9371	High Similarity	NPC103362
0.9371	High Similarity	NPC17170
0.9371	High Similarity	NPC156190
0.9371	High Similarity	NPC321980
0.9371	High Similarity	NPC156590
0.9371	High Similarity	NPC205006
0.9371	High Similarity	NPC118840
0.9371	High Similarity	NPC470089
0.9371	High Similarity	NPC470087
0.9371	High Similarity	NPC279650
0.9371	High Similarity	NPC312391
0.9371	High Similarity	NPC213322
0.9371	High Similarity	NPC110038
0.9371	High Similarity	NPC166689
0.9371	High Similarity	NPC3188
0.9371	High Similarity	NPC258630
0.9371	High Similarity	NPC64908
0.9371	High Similarity	NPC282300

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 NPC317492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	956
0.2-0.3	1536
0.3-0.4	2599
0.4-0.5	2000
0.5-0.6	1155
0.6-0.7	365
0.7-0.8	124
0.8-0.85	48
0.85-0.9	19
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD4378	Clinical (unspecified phase)
0.9161	High Similarity	NPD1549	Phase 2
0.9155	High Similarity	NPD2796	Approved
0.9128	High Similarity	NPD4380	Phase 2
0.9091	High Similarity	NPD1552	Clinical (unspecified phase)
0.9091	High Similarity	NPD1550	Clinical (unspecified phase)
0.9085	High Similarity	NPD1510	Phase 2
0.9073	High Similarity	NPD2393	Clinical (unspecified phase)
0.9048	High Similarity	NPD7410	Clinical (unspecified phase)
0.8896	High Similarity	NPD7075	Discontinued
0.8889	High Similarity	NPD8443	Clinical (unspecified phase)
0.8824	High Similarity	NPD7096	Clinical (unspecified phase)
0.8816	High Similarity	NPD7411	Suspended
0.8803	High Similarity	NPD1240	Approved
0.8774	High Similarity	NPD4381	Clinical (unspecified phase)
0.8758	High Similarity	NPD6801	Discontinued
0.8758	High Similarity	NPD1934	Approved
0.871	High Similarity	NPD3882	Suspended
0.8707	High Similarity	NPD2800	Approved
0.8701	High Similarity	NPD2801	Approved
0.8701	High Similarity	NPD7819	Suspended
0.8688	High Similarity	NPD3818	Discontinued
0.8681	High Similarity	NPD1607	Approved
0.8675	High Similarity	NPD920	Approved
0.8662	High Similarity	NPD5494	Approved
0.86	High Similarity	NPD1511	Approved
0.8543	High Similarity	NPD642	Clinical (unspecified phase)
0.8519	High Similarity	NPD7804	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6959	Discontinued
0.8487	Intermediate Similarity	NPD1512	Approved
0.8477	Intermediate Similarity	NPD6799	Approved
0.8471	Intermediate Similarity	NPD7768	Phase 2
0.8456	Intermediate Similarity	NPD1243	Approved
0.8456	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD2533	Approved
0.8421	Intermediate Similarity	NPD2532	Approved
0.8421	Intermediate Similarity	NPD2534	Approved
0.8418	Intermediate Similarity	NPD3749	Approved
0.8411	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD3750	Approved
0.8364	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2344	Approved
0.8313	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD3817	Phase 2
0.8276	Intermediate Similarity	NPD2313	Discontinued
0.8269	Intermediate Similarity	NPD6599	Discontinued
0.8255	Intermediate Similarity	NPD2935	Discontinued
0.8255	Intermediate Similarity	NPD1551	Phase 2
0.8239	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD5403	Approved
0.8193	Intermediate Similarity	NPD5953	Discontinued
0.8188	Intermediate Similarity	NPD2799	Discontinued
0.8182	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD7286	Phase 2
0.8176	Intermediate Similarity	NPD5402	Approved
0.8158	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1247	Approved
0.8146	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8105	Intermediate Similarity	NPD2309	Approved
0.8098	Intermediate Similarity	NPD6232	Discontinued
0.8084	Intermediate Similarity	NPD6797	Phase 2
0.8067	Intermediate Similarity	NPD3748	Approved
0.8065	Intermediate Similarity	NPD5401	Approved
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8054	Intermediate Similarity	NPD6651	Approved
0.8036	Intermediate Similarity	NPD7251	Discontinued
0.8025	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD7808	Phase 3
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3226	Approved
0.7964	Intermediate Similarity	NPD5844	Phase 1
0.7947	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7033	Discontinued
0.7922	Intermediate Similarity	NPD4628	Phase 3
0.7905	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.7841	Intermediate Similarity	NPD4363	Phase 3
0.7841	Intermediate Similarity	NPD4360	Phase 2
0.7831	Intermediate Similarity	NPD3926	Phase 2
0.7808	Intermediate Similarity	NPD1203	Approved
0.78	Intermediate Similarity	NPD943	Approved
0.7797	Intermediate Similarity	NPD4361	Phase 2
0.7797	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5710	Approved
0.7771	Intermediate Similarity	NPD5711	Approved
0.777	Intermediate Similarity	NPD6832	Phase 2
0.777	Intermediate Similarity	NPD4908	Phase 1
0.7765	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2798	Approved
0.7746	Intermediate Similarity	NPD1548	Phase 1
0.7727	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1729	Discontinued
0.7667	Intermediate Similarity	NPD3268	Approved
0.7665	Intermediate Similarity	NPD7229	Phase 3
0.7662	Intermediate Similarity	NPD6100	Approved
0.7662	Intermediate Similarity	NPD6099	Approved
0.7658	Intermediate Similarity	NPD7390	Discontinued
0.7655	Intermediate Similarity	NPD1610	Phase 2
0.7654	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5124	Phase 1
0.7628	Intermediate Similarity	NPD2654	Approved
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD9717	Approved
0.7597	Intermediate Similarity	NPD4308	Phase 3
0.7588	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2797	Approved
0.7561	Intermediate Similarity	NPD1465	Phase 2
0.7561	Intermediate Similarity	NPD5760	Phase 2
0.7561	Intermediate Similarity	NPD5761	Phase 2
0.755	Intermediate Similarity	NPD3764	Approved
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7515	Intermediate Similarity	NPD2296	Approved
0.75	Intermediate Similarity	NPD6844	Discontinued
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7473	Intermediate Similarity	NPD7584	Approved
0.7452	Intermediate Similarity	NPD2424	Discontinued
0.7451	Intermediate Similarity	NPD1613	Approved
0.7451	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8313	Approved
0.7429	Intermediate Similarity	NPD8312	Approved
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.7416	Intermediate Similarity	NPD4287	Approved
0.741	Intermediate Similarity	NPD4288	Approved
0.7403	Intermediate Similarity	NPD447	Suspended
0.7394	Intermediate Similarity	NPD37	Approved
0.7394	Intermediate Similarity	NPD6280	Approved
0.7394	Intermediate Similarity	NPD6279	Approved
0.7389	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6002	Phase 3
0.7389	Intermediate Similarity	NPD6004	Phase 3
0.7389	Intermediate Similarity	NPD6005	Phase 3
0.7389	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3751	Discontinued
0.7383	Intermediate Similarity	NPD3225	Approved
0.7381	Intermediate Similarity	NPD6234	Discontinued
0.7379	Intermediate Similarity	NPD9545	Approved
0.7368	Intermediate Similarity	NPD2403	Approved
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7365	Intermediate Similarity	NPD4967	Phase 2
0.7365	Intermediate Similarity	NPD4965	Approved
0.7365	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD3972	Approved
0.7353	Intermediate Similarity	NPD6808	Phase 2
0.7351	Intermediate Similarity	NPD2861	Phase 2
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.7333	Intermediate Similarity	NPD3267	Approved
0.7333	Intermediate Similarity	NPD5889	Approved
0.7333	Intermediate Similarity	NPD5890	Approved
0.7333	Intermediate Similarity	NPD3266	Approved
0.7333	Intermediate Similarity	NPD1470	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6798	Discontinued
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.729	Intermediate Similarity	NPD1933	Approved
0.729	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD1019	Discontinued
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7267	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3027	Phase 3
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.725	Intermediate Similarity	NPD7003	Approved
0.7248	Intermediate Similarity	NPD1608	Approved
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7241	Intermediate Similarity	NPD9493	Approved
0.7239	Intermediate Similarity	NPD6273	Approved
0.7237	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1164	Approved
0.7216	Intermediate Similarity	NPD6104	Discontinued
0.7216	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5408	Approved
0.7215	Intermediate Similarity	NPD5404	Approved
0.7215	Intermediate Similarity	NPD5405	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