NPASS Compound

Structure

NPC184797 OpenBabel07101719402D 22 25 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 -2.5981 1.5000 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 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 -0.8660 1.5000 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 5.6667 -0.6226 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 -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 20 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 21 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 14 2 0 0 0 0 11 16 2 0 0 0 0 12 8 1 6 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 11 1 6 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	296.495
LogP:	2.971
LogD:	2.987
LogS:	-3.994
# Rotatable Bonds:	2
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.924
Synthetic Accessibility Score:	3.354
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.733
MDCK Permeability:	2.3268754375749268e-05
Pgp-inhibitor:	0.45
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	97.9424057006836%
Volume Distribution (VD):	0.533
Pgp-substrate:	4.870913028717041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.832
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.893
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.606
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.81

ADMET: Excretion

Clearance (CL):	3.135
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.183
Human Hepatotoxicity (H-HT):	0.495
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.87
Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.88
Skin Sensitization:	0.867
Carcinogencity:	0.406
Eye Corrosion:	0.003
Eye Irritation:	0.741
Respiratory Toxicity:	0.673

Download Data

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

Natural Product: NPC184797

Natural Product ID:	NPC184797
*Common Name:**	(6Ar,11Ar)-4-Methoxymedicarpin
IUPAC Name:	(6aR,11aR)-4,9-dimethoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol
Synonyms:	(6Ar,11Ar)-4-Methoxymedicarpin
Standard InCHIKey:	IPDALSAPRYQWGQ-WFASDCNBSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-19-9-3-4-10-12-8-21-16-11(15(12)22-14(10)7-9)5-6-13(18)17(16)20-2/h3-7,12,15,18H,8H2,1-2H3/t12-,15-/m0/s1
SMILES:	COc1ccc2[C@@H]3COc4c(ccc(c4OC)O)[C@@H]3Oc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404648
PubChem CID:	14077266
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
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	6
Others	1

Activity Type	# Activity
Cell Line	4
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	>	100.0	uM	PMID[538454]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	97300.0	nM	PMID[538455]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	47100.0	nM	PMID[538455]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	96300.0	nM	PMID[538455]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[538455]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	97600.0	nM	PMID[538455]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29400.0	nM	PMID[538455]

☑ 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 NPC184797 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	NPC309124
0.9924	High Similarity	NPC236306
0.9924	High Similarity	NPC473739
0.9924	High Similarity	NPC232164
0.9851	High Similarity	NPC107161
0.9776	High Similarity	NPC247291
0.9773	High Similarity	NPC162659
0.9773	High Similarity	NPC270456
0.9773	High Similarity	NPC248727
0.9773	High Similarity	NPC265433
0.9706	High Similarity	NPC45257
0.9706	High Similarity	NPC12641
0.9706	High Similarity	NPC280092
0.9706	High Similarity	NPC93323
0.9701	High Similarity	NPC254759
0.9701	High Similarity	NPC160283
0.9701	High Similarity	NPC27495
0.9697	High Similarity	NPC470356
0.9697	High Similarity	NPC121812
0.9697	High Similarity	NPC112246
0.9697	High Similarity	NPC94750
0.9697	High Similarity	NPC112939
0.9697	High Similarity	NPC474206
0.9632	High Similarity	NPC85264
0.9632	High Similarity	NPC102044
0.9632	High Similarity	NPC47633
0.963	High Similarity	NPC87725
0.963	High Similarity	NPC471389
0.963	High Similarity	NPC263261
0.9627	High Similarity	NPC292882
0.9627	High Similarity	NPC25966
0.9627	High Similarity	NPC70682
0.9627	High Similarity	NPC260741
0.9627	High Similarity	NPC245207
0.9627	High Similarity	NPC127218
0.9627	High Similarity	NPC319647
0.9624	High Similarity	NPC306441
0.9624	High Similarity	NPC230734
0.9624	High Similarity	NPC474639
0.9624	High Similarity	NPC227503
0.9624	High Similarity	NPC16435
0.9621	High Similarity	NPC317380
0.9562	High Similarity	NPC63879
0.9552	High Similarity	NPC176051
0.9552	High Similarity	NPC107551
0.9552	High Similarity	NPC211549
0.9552	High Similarity	NPC276490
0.9552	High Similarity	NPC103976
0.9552	High Similarity	NPC474282
0.9552	High Similarity	NPC102904
0.9552	High Similarity	NPC326797
0.9549	High Similarity	NPC47398
0.9549	High Similarity	NPC260898
0.9549	High Similarity	NPC61946
0.9549	High Similarity	NPC234333
0.9549	High Similarity	NPC151224
0.9545	High Similarity	NPC158331
0.9545	High Similarity	NPC11060
0.9496	High Similarity	NPC21776
0.9496	High Similarity	NPC16269
0.9489	High Similarity	NPC81638
0.9489	High Similarity	NPC477616
0.9485	High Similarity	NPC35216
0.9485	High Similarity	NPC311530
0.9481	High Similarity	NPC471388
0.9478	High Similarity	NPC302701
0.9478	High Similarity	NPC173660
0.9478	High Similarity	NPC269091
0.9478	High Similarity	NPC234952
0.9474	High Similarity	NPC287745
0.9474	High Similarity	NPC478085
0.947	High Similarity	NPC86655
0.947	High Similarity	NPC127624
0.947	High Similarity	NPC204215
0.947	High Similarity	NPC175067
0.947	High Similarity	NPC202762
0.9424	High Similarity	NPC324492
0.9424	High Similarity	NPC260397
0.9424	High Similarity	NPC317053
0.942	High Similarity	NPC473108
0.9416	High Similarity	NPC2613
0.9416	High Similarity	NPC204347
0.9416	High Similarity	NPC475891
0.9416	High Similarity	NPC59841
0.9412	High Similarity	NPC259519
0.9407	High Similarity	NPC477938
0.9403	High Similarity	NPC164787
0.9403	High Similarity	NPC126409
0.9403	High Similarity	NPC134968
0.9403	High Similarity	NPC473413
0.9403	High Similarity	NPC99572
0.9403	High Similarity	NPC195022
0.9398	High Similarity	NPC168059
0.9398	High Similarity	NPC229442
0.9398	High Similarity	NPC475840
0.9398	High Similarity	NPC263064
0.9357	High Similarity	NPC320671
0.9357	High Similarity	NPC328567
0.9357	High Similarity	NPC101376
0.9357	High Similarity	NPC327412
0.9357	High Similarity	NPC320970
0.9353	High Similarity	NPC307466
0.9353	High Similarity	NPC469557
0.9343	High Similarity	NPC178054
0.9338	High Similarity	NPC32630
0.9333	High Similarity	NPC177160
0.9333	High Similarity	NPC10737
0.9333	High Similarity	NPC209985
0.9333	High Similarity	NPC156502
0.9333	High Similarity	NPC470802
0.9333	High Similarity	NPC263367
0.9333	High Similarity	NPC472334
0.9333	High Similarity	NPC29799
0.9333	High Similarity	NPC472336
0.9333	High Similarity	NPC477939
0.9333	High Similarity	NPC54743
0.9328	High Similarity	NPC49603
0.9328	High Similarity	NPC170694
0.9328	High Similarity	NPC326095
0.9328	High Similarity	NPC244983
0.9328	High Similarity	NPC193026
0.9328	High Similarity	NPC474478
0.9328	High Similarity	NPC187616
0.9323	High Similarity	NPC219876
0.9323	High Similarity	NPC126029
0.9323	High Similarity	NPC261619
0.9323	High Similarity	NPC201587
0.9323	High Similarity	NPC61477
0.9323	High Similarity	NPC253105
0.9323	High Similarity	NPC185604
0.9323	High Similarity	NPC78770
0.9323	High Similarity	NPC15658
0.9291	High Similarity	NPC166584
0.9291	High Similarity	NPC301961
0.9286	High Similarity	NPC87794
0.9286	High Similarity	NPC211758
0.9281	High Similarity	NPC471415
0.9281	High Similarity	NPC50250
0.9281	High Similarity	NPC114119
0.9281	High Similarity	NPC470097
0.927	High Similarity	NPC266197
0.927	High Similarity	NPC291101
0.927	High Similarity	NPC22317
0.9259	High Similarity	NPC165155
0.9259	High Similarity	NPC34103
0.9259	High Similarity	NPC24490
0.9259	High Similarity	NPC141765
0.9259	High Similarity	NPC472337
0.9248	High Similarity	NPC474017
0.9248	High Similarity	NPC42760
0.9248	High Similarity	NPC220825
0.9248	High Similarity	NPC162801
0.9248	High Similarity	NPC268342
0.9248	High Similarity	NPC268266
0.9248	High Similarity	NPC472597
0.922	High Similarity	NPC39657
0.9214	High Similarity	NPC181615
0.9209	High Similarity	NPC163508
0.9209	High Similarity	NPC173203
0.9203	High Similarity	NPC265075
0.9197	High Similarity	NPC292487
0.9197	High Similarity	NPC22517
0.9191	High Similarity	NPC78047
0.9185	High Similarity	NPC106215
0.9185	High Similarity	NPC117048
0.9185	High Similarity	NPC124085
0.9179	High Similarity	NPC160991
0.9179	High Similarity	NPC35932
0.9179	High Similarity	NPC470752
0.9179	High Similarity	NPC184447
0.9179	High Similarity	NPC6451
0.9179	High Similarity	NPC7903
0.9179	High Similarity	NPC16208
0.9173	High Similarity	NPC153739
0.9173	High Similarity	NPC472338
0.9173	High Similarity	NPC92164
0.9173	High Similarity	NPC257582
0.9173	High Similarity	NPC242807
0.9173	High Similarity	NPC241522
0.9173	High Similarity	NPC91291
0.9173	High Similarity	NPC187998
0.9173	High Similarity	NPC77040
0.9173	High Similarity	NPC145305
0.9173	High Similarity	NPC64201
0.9173	High Similarity	NPC174495
0.9173	High Similarity	NPC42300
0.9167	High Similarity	NPC282703
0.9167	High Similarity	NPC21867
0.9167	High Similarity	NPC47283
0.9167	High Similarity	NPC45774
0.9167	High Similarity	NPC39064
0.9167	High Similarity	NPC11258
0.9167	High Similarity	NPC226331
0.9167	High Similarity	NPC46274
0.9167	High Similarity	NPC160196
0.9167	High Similarity	NPC128208
0.9167	High Similarity	NPC31707
0.9167	High Similarity	NPC129570
0.9167	High Similarity	NPC184733
0.9161	High Similarity	NPC472709

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 NPC184797 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
0.9323	High Similarity	NPD1612	Clinical (unspecified phase)
0.9323	High Similarity	NPD1613	Approved
0.9167	High Similarity	NPD1529	Clinical (unspecified phase)
0.9098	High Similarity	NPD3027	Phase 3
0.9091	High Similarity	NPD1530	Clinical (unspecified phase)
0.8741	High Similarity	NPD4908	Phase 1
0.8636	High Similarity	NPD1610	Phase 2
0.8613	High Similarity	NPD4907	Clinical (unspecified phase)
0.8529	High Similarity	NPD2861	Phase 2
0.8467	Intermediate Similarity	NPD1934	Approved
0.8289	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4749	Approved
0.8195	Intermediate Similarity	NPD1548	Phase 1
0.8194	Intermediate Similarity	NPD6234	Discontinued
0.8143	Intermediate Similarity	NPD4625	Phase 3
0.8085	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1653	Approved
0.8065	Intermediate Similarity	NPD3882	Suspended
0.8065	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2801	Approved
0.805	Intermediate Similarity	NPD6166	Phase 2
0.805	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3018	Phase 2
0.7987	Intermediate Similarity	NPD37	Approved
0.7975	Intermediate Similarity	NPD7199	Phase 2
0.7955	Intermediate Similarity	NPD5283	Phase 1
0.795	Intermediate Similarity	NPD3818	Discontinued
0.795	Intermediate Similarity	NPD7228	Approved
0.7949	Intermediate Similarity	NPD4965	Approved
0.7949	Intermediate Similarity	NPD4967	Phase 2
0.7949	Intermediate Similarity	NPD4966	Approved
0.7911	Intermediate Similarity	NPD5494	Approved
0.7905	Intermediate Similarity	NPD6674	Discontinued
0.7905	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7074	Phase 3
0.7847	Intermediate Similarity	NPD3620	Phase 2
0.7847	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4060	Phase 1
0.7842	Intermediate Similarity	NPD2983	Phase 2
0.7842	Intermediate Similarity	NPD2982	Phase 2
0.7815	Intermediate Similarity	NPD1511	Approved
0.7803	Intermediate Similarity	NPD228	Approved
0.7791	Intermediate Similarity	NPD7054	Approved
0.777	Intermediate Similarity	NPD2981	Phase 2
0.7744	Intermediate Similarity	NPD7472	Approved
0.7712	Intermediate Similarity	NPD1512	Approved
0.7698	Intermediate Similarity	NPD1091	Approved
0.7698	Intermediate Similarity	NPD3705	Approved
0.7683	Intermediate Similarity	NPD5844	Phase 1
0.7658	Intermediate Similarity	NPD3817	Phase 2
0.7652	Intermediate Similarity	NPD3021	Approved
0.7652	Intermediate Similarity	NPD3022	Approved
0.7651	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD5588	Approved
0.7603	Intermediate Similarity	NPD1558	Phase 1
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7589	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD6099	Approved
0.7582	Intermediate Similarity	NPD7213	Phase 3
0.7582	Intermediate Similarity	NPD7212	Phase 2
0.7574	Intermediate Similarity	NPD6671	Approved
0.7568	Intermediate Similarity	NPD4538	Approved
0.7568	Intermediate Similarity	NPD4536	Approved
0.7568	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6355	Discontinued
0.7551	Intermediate Similarity	NPD5124	Phase 1
0.755	Intermediate Similarity	NPD5177	Phase 3
0.755	Intermediate Similarity	NPD1652	Phase 2
0.7547	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7535	Intermediate Similarity	NPD8651	Approved
0.7533	Intermediate Similarity	NPD7266	Discontinued
0.7533	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7447	Phase 1
0.7517	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5058	Phase 3
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD4675	Approved
0.7516	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD2489	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD7466	Approved
0.75	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD3892	Phase 2
0.75	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD27	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1549	Phase 2
0.7465	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7310	Approved
0.7456	Intermediate Similarity	NPD4578	Approved
0.7456	Intermediate Similarity	NPD7311	Approved
0.7456	Intermediate Similarity	NPD7313	Approved
0.7456	Intermediate Similarity	NPD7312	Approved
0.7456	Intermediate Similarity	NPD4577	Approved
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7453	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD422	Phase 1
0.7445	Intermediate Similarity	NPD7157	Approved
0.7444	Intermediate Similarity	NPD2684	Approved
0.744	Intermediate Similarity	NPD7240	Approved
0.744	Intermediate Similarity	NPD6559	Discontinued
0.7439	Intermediate Similarity	NPD2970	Approved
0.7439	Intermediate Similarity	NPD2969	Approved
0.7438	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5735	Approved
0.7427	Intermediate Similarity	NPD4663	Approved
0.7419	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5763	Approved
0.7417	Intermediate Similarity	NPD5762	Approved
0.7417	Intermediate Similarity	NPD3540	Phase 1
0.7412	Intermediate Similarity	NPD7309	Approved
0.7412	Intermediate Similarity	NPD8053	Approved
0.7412	Intermediate Similarity	NPD8054	Approved
0.74	Intermediate Similarity	NPD5960	Phase 3
0.7386	Intermediate Similarity	NPD4110	Phase 3
0.7386	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7906	Approved
0.7378	Intermediate Similarity	NPD6232	Discontinued
0.7378	Intermediate Similarity	NPD3051	Approved
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD290	Approved
0.7368	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1357	Approved
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7843	Approved
0.7351	Intermediate Similarity	NPD3539	Phase 1
0.7349	Intermediate Similarity	NPD7473	Discontinued
0.7347	Intermediate Similarity	NPD6798	Discontinued
0.7342	Intermediate Similarity	NPD4005	Discontinued
0.7338	Intermediate Similarity	NPD2677	Approved
0.7329	Intermediate Similarity	NPD2563	Approved
0.7329	Intermediate Similarity	NPD2560	Approved
0.732	Intermediate Similarity	NPD4237	Approved
0.732	Intermediate Similarity	NPD4236	Phase 3
0.731	Intermediate Similarity	NPD6584	Phase 3
0.7308	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1375	Discontinued
0.7292	Intermediate Similarity	NPD6696	Suspended
0.729	Intermediate Similarity	NPD7124	Phase 2
0.7279	Intermediate Similarity	NPD7095	Approved
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD6071	Discontinued
0.7273	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7259	Intermediate Similarity	NPD4750	Phase 3
0.7255	Intermediate Similarity	NPD2424	Discontinued
0.7248	Intermediate Similarity	NPD2238	Phase 2
0.7244	Intermediate Similarity	NPD4357	Discontinued
0.7237	Intermediate Similarity	NPD2796	Approved
0.7237	Intermediate Similarity	NPD2161	Phase 2
0.7222	Intermediate Similarity	NPD5327	Phase 3
0.7215	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6959	Discontinued
0.7209	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3060	Approved
0.7197	Intermediate Similarity	NPD4123	Phase 3
0.7183	Intermediate Similarity	NPD6516	Phase 2
0.7183	Intermediate Similarity	NPD5846	Approved
0.7181	Intermediate Similarity	NPD6233	Phase 2
0.7171	Intermediate Similarity	NPD1510	Phase 2
0.7171	Intermediate Similarity	NPD7033	Discontinued
0.7169	Intermediate Similarity	NPD3787	Discontinued
0.7164	Intermediate Similarity	NPD968	Approved
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD5773	Approved
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2978	Approved
0.716	Intermediate Similarity	NPD2977	Approved
0.716	Intermediate Similarity	NPD5772	Approved
0.7152	Intermediate Similarity	NPD6653	Approved
0.7152	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1774	Approved
0.7134	Intermediate Similarity	NPD6799	Approved
0.7133	Intermediate Similarity	NPD4140	Approved
0.7133	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3926	Phase 2
0.7123	Intermediate Similarity	NPD2797	Approved
0.7123	Intermediate Similarity	NPD3094	Phase 2
0.7121	Intermediate Similarity	NPD846	Approved
0.7121	Intermediate Similarity	NPD940	Approved
0.7117	Intermediate Similarity	NPD5402	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