NPASS Compound

Structure

NPC232164 OpenBabel07101718192D 21 24 0 0 1 0 0 0 0 0999 V2000 6.2545 0.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0898 -1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 0.3955 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 4.6722 -0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 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 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6667 -0.6226 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 2.6831 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 20 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 16 2 0 0 0 0 11 7 1 6 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 10 1 6 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	279.199
LogP:	2.698
LogD:	2.553
LogS:	-3.873
# Rotatable Bonds:	1
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	3.355
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.923
MDCK Permeability:	1.185413020721171e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	98.87848663330078%
Volume Distribution (VD):	0.506
Pgp-substrate:	3.843402147293091%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.751
CYP2C19-substrate:	0.564
CYP2C9-inhibitor:	0.842
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.615
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.534

ADMET: Excretion

Clearance (CL):	5.146
Half-life (T1/2):	0.447

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.714
Drug-inuced Liver Injury (DILI):	0.886
AMES Toxicity:	0.889
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.921
Carcinogencity:	0.585
Eye Corrosion:	0.003
Eye Irritation:	0.864
Respiratory Toxicity:	0.553

Download Data

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

Natural Product: NPC232164

Natural Product ID:	NPC232164
*Common Name:**	4-Hydroxymedicarpin
IUPAC Name:	(6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,4-diol
Synonyms:	4-Hydroxymedicarpin
Standard InCHIKey:	YRFDJOAWSXSLMG-NHYWBVRUSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-19-8-2-3-9-11-7-20-16-10(4-5-12(17)14(16)18)15(11)21-13(9)6-8/h2-6,11,15,17-18H,7H2,1H3/t11-,15-/m0/s1
SMILES:	COc1ccc2c(c1)O[C@@H]1[C@H]2COc2c1ccc(c2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253466
PubChem CID:	13940834
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO29804	Nepalese propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15974608]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]

☑ 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	7
Others	1

Activity Type	# Activity
Cell Line	4
CELL-LINE	1
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	=	25.0	uM	PMID[497612]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[497613]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[497613]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[497613]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[497613]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	54100.0	nM	PMID[497613]
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	5400.0	nM	PMID[497614]

☑ 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 NPC232164 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	432
0.1-0.2	1600
0.2-0.3	4450
0.3-0.4	12181
0.4-0.5	5994
0.5-0.6	4039
0.6-0.7	6399
0.7-0.8	5600
0.8-0.85	1015
0.85-0.9	704
0.9-0.95	239
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473739
1.0	High Similarity	NPC236306
0.9924	High Similarity	NPC309124
0.9924	High Similarity	NPC184797
0.9776	High Similarity	NPC107161
0.9701	High Similarity	NPC247291
0.9697	High Similarity	NPC248727
0.9697	High Similarity	NPC270456
0.9697	High Similarity	NPC162659
0.9697	High Similarity	NPC265433
0.9632	High Similarity	NPC280092
0.9632	High Similarity	NPC93323
0.9632	High Similarity	NPC12641
0.9632	High Similarity	NPC45257
0.9627	High Similarity	NPC254759
0.9627	High Similarity	NPC160283
0.9627	High Similarity	NPC27495
0.9621	High Similarity	NPC112939
0.9621	High Similarity	NPC474206
0.9621	High Similarity	NPC112246
0.9621	High Similarity	NPC121812
0.9621	High Similarity	NPC470356
0.9621	High Similarity	NPC94750
0.9559	High Similarity	NPC85264
0.9559	High Similarity	NPC102044
0.9559	High Similarity	NPC47633
0.9556	High Similarity	NPC263261
0.9556	High Similarity	NPC471389
0.9556	High Similarity	NPC87725
0.9552	High Similarity	NPC319647
0.9552	High Similarity	NPC70682
0.9552	High Similarity	NPC245207
0.9552	High Similarity	NPC292882
0.9552	High Similarity	NPC25966
0.9552	High Similarity	NPC127218
0.9552	High Similarity	NPC260741
0.9549	High Similarity	NPC306441
0.9549	High Similarity	NPC230734
0.9549	High Similarity	NPC474639
0.9549	High Similarity	NPC227503
0.9549	High Similarity	NPC16435
0.9545	High Similarity	NPC317380
0.9542	High Similarity	NPC202762
0.9542	High Similarity	NPC86655
0.9489	High Similarity	NPC63879
0.9478	High Similarity	NPC474282
0.9478	High Similarity	NPC176051
0.9478	High Similarity	NPC103976
0.9478	High Similarity	NPC102904
0.9478	High Similarity	NPC107551
0.9478	High Similarity	NPC276490
0.9478	High Similarity	NPC326797
0.9478	High Similarity	NPC211549
0.9474	High Similarity	NPC47398
0.9474	High Similarity	NPC151224
0.9474	High Similarity	NPC61946
0.9474	High Similarity	NPC260898
0.9474	High Similarity	NPC234333
0.947	High Similarity	NPC158331
0.947	High Similarity	NPC11060
0.9424	High Similarity	NPC16269
0.9424	High Similarity	NPC21776
0.9416	High Similarity	NPC81638
0.9416	High Similarity	NPC477616
0.9412	High Similarity	NPC35216
0.9412	High Similarity	NPC311530
0.9407	High Similarity	NPC471388
0.9403	High Similarity	NPC234952
0.9403	High Similarity	NPC302701
0.9403	High Similarity	NPC269091
0.9403	High Similarity	NPC173660
0.9398	High Similarity	NPC478085
0.9398	High Similarity	NPC287745
0.9394	High Similarity	NPC126029
0.9394	High Similarity	NPC261619
0.9394	High Similarity	NPC185604
0.9394	High Similarity	NPC61477
0.9394	High Similarity	NPC78770
0.9394	High Similarity	NPC127624
0.9394	High Similarity	NPC219876
0.9394	High Similarity	NPC15658
0.9394	High Similarity	NPC175067
0.9394	High Similarity	NPC204215
0.9357	High Similarity	NPC166584
0.9357	High Similarity	NPC301961
0.9353	High Similarity	NPC317053
0.9353	High Similarity	NPC324492
0.9353	High Similarity	NPC260397
0.9348	High Similarity	NPC473108
0.9343	High Similarity	NPC2613
0.9343	High Similarity	NPC475891
0.9343	High Similarity	NPC59841
0.9343	High Similarity	NPC204347
0.9338	High Similarity	NPC259519
0.9333	High Similarity	NPC477938
0.9328	High Similarity	NPC164787
0.9328	High Similarity	NPC126409
0.9328	High Similarity	NPC473413
0.9328	High Similarity	NPC134968
0.9328	High Similarity	NPC99572
0.9328	High Similarity	NPC195022
0.9323	High Similarity	NPC475840
0.9323	High Similarity	NPC263064
0.9323	High Similarity	NPC229442
0.9323	High Similarity	NPC168059
0.9318	High Similarity	NPC268342
0.9318	High Similarity	NPC220825
0.9318	High Similarity	NPC42760
0.9318	High Similarity	NPC268266
0.9286	High Similarity	NPC320970
0.9286	High Similarity	NPC328567
0.9286	High Similarity	NPC101376
0.9286	High Similarity	NPC320671
0.9286	High Similarity	NPC327412
0.9281	High Similarity	NPC469557
0.9281	High Similarity	NPC307466
0.927	High Similarity	NPC178054
0.9265	High Similarity	NPC292487
0.9265	High Similarity	NPC32630
0.9259	High Similarity	NPC472334
0.9259	High Similarity	NPC477939
0.9259	High Similarity	NPC177160
0.9259	High Similarity	NPC54743
0.9259	High Similarity	NPC209985
0.9259	High Similarity	NPC156502
0.9259	High Similarity	NPC10737
0.9259	High Similarity	NPC472336
0.9259	High Similarity	NPC470802
0.9259	High Similarity	NPC263367
0.9259	High Similarity	NPC29799
0.9254	High Similarity	NPC49603
0.9254	High Similarity	NPC244983
0.9254	High Similarity	NPC474478
0.9254	High Similarity	NPC193026
0.9254	High Similarity	NPC187616
0.9254	High Similarity	NPC170694
0.9254	High Similarity	NPC326095
0.9254	High Similarity	NPC106215
0.9248	High Similarity	NPC201587
0.9248	High Similarity	NPC253105
0.9242	High Similarity	NPC91291
0.9237	High Similarity	NPC226331
0.9237	High Similarity	NPC47283
0.9237	High Similarity	NPC46274
0.9237	High Similarity	NPC39064
0.9214	High Similarity	NPC226540
0.9214	High Similarity	NPC87794
0.9214	High Similarity	NPC211758
0.9209	High Similarity	NPC50250
0.9209	High Similarity	NPC114119
0.9209	High Similarity	NPC317237
0.9209	High Similarity	NPC471415
0.9209	High Similarity	NPC470097
0.9209	High Similarity	NPC277951
0.9209	High Similarity	NPC44530
0.9197	High Similarity	NPC22317
0.9197	High Similarity	NPC266197
0.9197	High Similarity	NPC291101
0.9191	High Similarity	NPC94994
0.9185	High Similarity	NPC472337
0.9185	High Similarity	NPC24490
0.9185	High Similarity	NPC34103
0.9185	High Similarity	NPC141765
0.9185	High Similarity	NPC165155
0.9173	High Similarity	NPC472597
0.9173	High Similarity	NPC474017
0.9173	High Similarity	NPC162801
0.916	High Similarity	NPC250432
0.916	High Similarity	NPC5447
0.9149	High Similarity	NPC39657
0.9143	High Similarity	NPC11422
0.9143	High Similarity	NPC474749
0.9143	High Similarity	NPC181615
0.9143	High Similarity	NPC178014
0.9143	High Similarity	NPC42716
0.9137	High Similarity	NPC163508
0.9137	High Similarity	NPC135767
0.9137	High Similarity	NPC155392
0.9137	High Similarity	NPC173203
0.9137	High Similarity	NPC274721
0.913	High Similarity	NPC265075
0.9124	High Similarity	NPC22517
0.9118	High Similarity	NPC78047
0.9111	High Similarity	NPC117048
0.9111	High Similarity	NPC124085
0.9104	High Similarity	NPC16208
0.9104	High Similarity	NPC35932
0.9104	High Similarity	NPC470752
0.9104	High Similarity	NPC6451
0.9104	High Similarity	NPC160991
0.9104	High Similarity	NPC7903
0.9104	High Similarity	NPC184447
0.9098	High Similarity	NPC145305
0.9098	High Similarity	NPC42300
0.9098	High Similarity	NPC92164
0.9098	High Similarity	NPC241522
0.9098	High Similarity	NPC242807
0.9098	High Similarity	NPC472338
0.9098	High Similarity	NPC257582
0.9098	High Similarity	NPC187998

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 NPC232164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	877
0.2-0.3	1855
0.3-0.4	2725
0.4-0.5	1617
0.5-0.6	911
0.6-0.7	623
0.7-0.8	161
0.8-0.85	9
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9394	High Similarity	NPD1613	Approved
0.9394	High Similarity	NPD1612	Clinical (unspecified phase)
0.9237	High Similarity	NPD1529	Clinical (unspecified phase)
0.916	High Similarity	NPD1530	Clinical (unspecified phase)
0.9023	High Similarity	NPD3027	Phase 3
0.8702	High Similarity	NPD1610	Phase 2
0.8667	High Similarity	NPD4908	Phase 1
0.854	High Similarity	NPD4907	Clinical (unspecified phase)
0.8523	High Similarity	NPD1934	Approved
0.8456	Intermediate Similarity	NPD2861	Phase 2
0.8258	Intermediate Similarity	NPD1548	Phase 1
0.8224	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD4749	Approved
0.8129	Intermediate Similarity	NPD6234	Discontinued
0.8071	Intermediate Similarity	NPD4625	Phase 3
0.8014	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1653	Approved
0.8	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6166	Phase 2
0.7987	Intermediate Similarity	NPD2801	Approved
0.7987	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3018	Phase 2
0.7922	Intermediate Similarity	NPD37	Approved
0.7911	Intermediate Similarity	NPD7199	Phase 2
0.7888	Intermediate Similarity	NPD7228	Approved
0.7888	Intermediate Similarity	NPD3818	Discontinued
0.7885	Intermediate Similarity	NPD4967	Phase 2
0.7885	Intermediate Similarity	NPD4965	Approved
0.7885	Intermediate Similarity	NPD4966	Approved
0.7879	Intermediate Similarity	NPD5283	Phase 1
0.7867	Intermediate Similarity	NPD1511	Approved
0.7863	Intermediate Similarity	NPD228	Approved
0.7848	Intermediate Similarity	NPD5494	Approved
0.7838	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6674	Discontinued
0.7812	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD4060	Phase 1
0.7778	Intermediate Similarity	NPD3620	Phase 2
0.7778	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2982	Phase 2
0.777	Intermediate Similarity	NPD2983	Phase 2
0.7763	Intermediate Similarity	NPD1512	Approved
0.773	Intermediate Similarity	NPD7054	Approved
0.7698	Intermediate Similarity	NPD2981	Phase 2
0.7683	Intermediate Similarity	NPD7472	Approved
0.7655	Intermediate Similarity	NPD1558	Phase 1
0.7643	Intermediate Similarity	NPD1465	Phase 2
0.7626	Intermediate Similarity	NPD1091	Approved
0.7626	Intermediate Similarity	NPD3705	Approved
0.7622	Intermediate Similarity	NPD5844	Phase 1
0.7595	Intermediate Similarity	NPD3817	Phase 2
0.7584	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.7568	Intermediate Similarity	NPD5588	Approved
0.7533	Intermediate Similarity	NPD1549	Phase 2
0.753	Intermediate Similarity	NPD6797	Phase 2
0.7518	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7213	Phase 3
0.7516	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD4536	Approved
0.75	Intermediate Similarity	NPD4538	Approved
0.75	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7484	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD1652	Phase 2
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5177	Phase 3
0.7468	Intermediate Similarity	NPD7447	Phase 1
0.7467	Intermediate Similarity	NPD7266	Discontinued
0.7465	Intermediate Similarity	NPD8651	Approved
0.7452	Intermediate Similarity	NPD4380	Phase 2
0.7452	Intermediate Similarity	NPD4675	Approved
0.7452	Intermediate Similarity	NPD4678	Approved
0.7451	Intermediate Similarity	NPD5058	Phase 3
0.745	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7549	Discontinued
0.744	Intermediate Similarity	NPD7808	Phase 3
0.7439	Intermediate Similarity	NPD27	Approved
0.7439	Intermediate Similarity	NPD2489	Approved
0.7434	Intermediate Similarity	NPD3892	Phase 2
0.7434	Intermediate Similarity	NPD7466	Approved
0.7434	Intermediate Similarity	NPD6331	Phase 2
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD290	Approved
0.7419	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4577	Approved
0.7396	Intermediate Similarity	NPD7311	Approved
0.7396	Intermediate Similarity	NPD7312	Approved
0.7396	Intermediate Similarity	NPD7310	Approved
0.7396	Intermediate Similarity	NPD4578	Approved
0.7396	Intermediate Similarity	NPD7313	Approved
0.7394	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7075	Discontinued
0.7391	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6559	Discontinued
0.7381	Intermediate Similarity	NPD7240	Approved
0.7378	Intermediate Similarity	NPD2969	Approved
0.7378	Intermediate Similarity	NPD2970	Approved
0.7375	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7157	Approved
0.7368	Intermediate Similarity	NPD4663	Approved
0.7368	Intermediate Similarity	NPD2684	Approved
0.7365	Intermediate Similarity	NPD5735	Approved
0.7355	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8054	Approved
0.7353	Intermediate Similarity	NPD8053	Approved
0.7353	Intermediate Similarity	NPD7309	Approved
0.7351	Intermediate Similarity	NPD5763	Approved
0.7351	Intermediate Similarity	NPD5762	Approved
0.7351	Intermediate Similarity	NPD3540	Phase 1
0.7333	Intermediate Similarity	NPD5960	Phase 3
0.7326	Intermediate Similarity	NPD7906	Approved
0.732	Intermediate Similarity	NPD3750	Approved
0.732	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4110	Phase 3
0.732	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6232	Discontinued
0.7317	Intermediate Similarity	NPD3051	Approved
0.7312	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7473	Discontinued
0.7286	Intermediate Similarity	NPD1357	Approved
0.7285	Intermediate Similarity	NPD3539	Phase 1
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7279	Intermediate Similarity	NPD7843	Approved
0.7278	Intermediate Similarity	NPD4005	Discontinued
0.7273	Intermediate Similarity	NPD2677	Approved
0.7267	Intermediate Similarity	NPD2560	Approved
0.7267	Intermediate Similarity	NPD2563	Approved
0.7255	Intermediate Similarity	NPD4236	Phase 3
0.7255	Intermediate Similarity	NPD4237	Approved
0.7244	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6584	Phase 3
0.7237	Intermediate Similarity	NPD1375	Discontinued
0.7226	Intermediate Similarity	NPD7124	Phase 2
0.7222	Intermediate Similarity	NPD6696	Suspended
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7218	Intermediate Similarity	NPD968	Approved
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7212	Intermediate Similarity	NPD6071	Discontinued
0.7211	Intermediate Similarity	NPD7095	Approved
0.7205	Intermediate Similarity	NPD7819	Suspended
0.719	Intermediate Similarity	NPD2424	Discontinued
0.7185	Intermediate Similarity	NPD4750	Phase 3
0.7181	Intermediate Similarity	NPD2238	Phase 2
0.7179	Intermediate Similarity	NPD4357	Discontinued
0.7171	Intermediate Similarity	NPD2796	Approved
0.7171	Intermediate Similarity	NPD2161	Phase 2
0.7153	Intermediate Similarity	NPD5327	Phase 3
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6959	Discontinued
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3060	Approved
0.7134	Intermediate Similarity	NPD4123	Phase 3
0.7133	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD6233	Phase 2
0.7113	Intermediate Similarity	NPD6516	Phase 2
0.7113	Intermediate Similarity	NPD5846	Approved
0.7108	Intermediate Similarity	NPD3787	Discontinued
0.7105	Intermediate Similarity	NPD7033	Discontinued
0.7101	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2977	Approved
0.7099	Intermediate Similarity	NPD5772	Approved
0.7099	Intermediate Similarity	NPD1242	Phase 1
0.7099	Intermediate Similarity	NPD2978	Approved
0.7099	Intermediate Similarity	NPD5773	Approved
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7089	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6653	Approved
0.7083	Intermediate Similarity	NPD1608	Approved
0.7078	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1774	Approved
0.707	Intermediate Similarity	NPD6799	Approved
0.7067	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4140	Approved
0.7067	Intermediate Similarity	NPD1240	Approved
0.7066	Intermediate Similarity	NPD3926	Phase 2

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