NPASS Compound

Structure

NPC107627 OpenBabel07101719132D 42 47 0 0 1 0 0 0 0 0999 V2000 -4.2399 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 4.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.9792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8480 1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8480 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7839 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 5.3854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 2.4479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 2.4479 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 4 1 0 0 0 0 1 11 2 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 12 29 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 16 2 0 0 0 0 15 33 1 0 0 0 0 16 34 1 0 0 0 0 17 21 2 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 36 1 0 0 0 0 19 23 2 0 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 41 1 0 0 0 0 21 25 1 0 0 0 0 22 30 2 0 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 24 22 1 1 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 38 2 0 0 0 0 26 27 1 0 0 0 0 26 39 2 0 0 0 0 27 29 2 0 0 0 0 27 40 1 0 0 0 0 28 11 1 6 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.07
Volume:	317.409
LogP:	2.017
LogD:	1.727
LogS:	-2.598
# Rotatable Bonds:	6
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	2.431
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.205
MDCK Permeability:	1.2320521818764973e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.129
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	88.21025085449219%
Volume Distribution (VD):	0.469
Pgp-substrate:	8.351319313049316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.713
CYP2D6-inhibitor:	0.31
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.575
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	14.78
Half-life (T1/2):	0.96

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.649
AMES Toxicity:	0.403
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.893
Carcinogencity:	0.03
Eye Corrosion:	0.005
Eye Irritation:	0.882
Respiratory Toxicity:	0.096

Download Data

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

Natural Product: NPC107627

Natural Product ID:	NPC107627
*Common Name:**	Pancibiflavonol
IUPAC Name:	8-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
Synonyms:	Pancibiflavonol
Standard InCHIKey:	DNHKAECUBJUWGK-YWEHKCAJSA-N
Standard InCHI:	InChI=1S/C30H20O12/c31-13-4-1-11(2-5-13)28-24(25(38)21-17(35)8-14(32)9-20(21)41-28)22-18(36)10-19(37)23-26(39)27(40)29(42-30(22)23)12-3-6-15(33)16(34)7-12/h1-10,24,28,31-37,40H/t24-,28+/m1/s1
SMILES:	c1cc(ccc1[C@H]1[C@H](c2c(cc(c3c(=O)c(c(c4ccc(c(c4)O)O)oc23)O)O)O)C(=O)c2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504190
PubChem CID:	44575313
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO32446	calophyllum panciflorum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654415]

☑ 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	8

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[519039]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[519039]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	22.1	%	PMID[519039]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	50.2	%	PMID[519039]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	75.0	%	PMID[519039]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	94.4	%	PMID[519039]

☑ 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 NPC107627 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	545
0.1-0.2	2001
0.2-0.3	4690
0.3-0.4	10758
0.4-0.5	7037
0.5-0.6	3937
0.6-0.7	5254
0.7-0.8	4850
0.8-0.85	1991
0.85-0.9	1435
0.9-0.95	192
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC171985
0.9873	High Similarity	NPC320741
0.9752	High Similarity	NPC472454
0.9752	High Similarity	NPC257667
0.9752	High Similarity	NPC186847
0.9748	High Similarity	NPC224851
0.9565	High Similarity	NPC260266
0.9494	High Similarity	NPC295090
0.9437	High Similarity	NPC219927
0.9387	High Similarity	NPC475212
0.9379	High Similarity	NPC63438
0.9375	High Similarity	NPC289771
0.9367	High Similarity	NPC32867
0.9329	High Similarity	NPC279209
0.9329	High Similarity	NPC102277
0.9321	High Similarity	NPC259757
0.9317	High Similarity	NPC477841
0.9268	High Similarity	NPC300307
0.9255	High Similarity	NPC142252
0.925	High Similarity	NPC123544
0.925	High Similarity	NPC117418
0.925	High Similarity	NPC53545
0.9245	High Similarity	NPC69531
0.9231	High Similarity	NPC132111
0.9226	High Similarity	NPC324742
0.9207	High Similarity	NPC295082
0.9202	High Similarity	NPC477840
0.9202	High Similarity	NPC7154
0.9202	High Similarity	NPC36916
0.9202	High Similarity	NPC36
0.9202	High Similarity	NPC62261
0.9202	High Similarity	NPC125039
0.9202	High Similarity	NPC7688
0.9202	High Similarity	NPC72787
0.9202	High Similarity	NPC58223
0.9198	High Similarity	NPC474150
0.9198	High Similarity	NPC474162
0.9182	High Similarity	NPC182555
0.9182	High Similarity	NPC66441
0.9177	High Similarity	NPC174086
0.9162	High Similarity	NPC99591
0.9157	High Similarity	NPC4200
0.9152	High Similarity	NPC177480
0.9146	High Similarity	NPC272560
0.9141	High Similarity	NPC12461
0.9141	High Similarity	NPC472625
0.9141	High Similarity	NPC476295
0.9136	High Similarity	NPC471499
0.9136	High Similarity	NPC305987
0.9136	High Similarity	NPC113163
0.9136	High Similarity	NPC312273
0.9136	High Similarity	NPC26326
0.9136	High Similarity	NPC165970
0.9136	High Similarity	NPC301256
0.9136	High Similarity	NPC66618
0.9136	High Similarity	NPC288131
0.9136	High Similarity	NPC84324
0.913	High Similarity	NPC22192
0.9119	High Similarity	NPC192083
0.9119	High Similarity	NPC213896
0.9091	High Similarity	NPC243877
0.908	High Similarity	NPC473011
0.908	High Similarity	NPC206605
0.908	High Similarity	NPC473012
0.908	High Similarity	NPC476247
0.9074	High Similarity	NPC118256
0.9074	High Similarity	NPC101731
0.9074	High Similarity	NPC297212
0.9074	High Similarity	NPC282009
0.9074	High Similarity	NPC119209
0.9074	High Similarity	NPC192686
0.9074	High Similarity	NPC287328
0.9074	High Similarity	NPC470326
0.9068	High Similarity	NPC112954
0.9068	High Similarity	NPC475184
0.9068	High Similarity	NPC471209
0.9062	High Similarity	NPC321779
0.9062	High Similarity	NPC134171
0.9062	High Similarity	NPC258474
0.9062	High Similarity	NPC133392
0.9062	High Similarity	NPC300668
0.9062	High Similarity	NPC201227
0.9057	High Similarity	NPC157784
0.9057	High Similarity	NPC106976
0.9057	High Similarity	NPC37684
0.9057	High Similarity	NPC63187
0.9053	High Similarity	NPC265380
0.9042	High Similarity	NPC212038
0.9042	High Similarity	NPC81332
0.9042	High Similarity	NPC262580
0.9042	High Similarity	NPC271848
0.9042	High Similarity	NPC289396
0.9036	High Similarity	NPC188079
0.903	High Similarity	NPC207575
0.903	High Similarity	NPC82330
0.903	High Similarity	NPC471213
0.903	High Similarity	NPC120593
0.903	High Similarity	NPC13481
0.9024	High Similarity	NPC272064
0.9024	High Similarity	NPC290160
0.9024	High Similarity	NPC186686
0.9024	High Similarity	NPC473009
0.9024	High Similarity	NPC41301
0.9018	High Similarity	NPC474038
0.9018	High Similarity	NPC266314
0.9018	High Similarity	NPC34089
0.9018	High Similarity	NPC196179
0.9018	High Similarity	NPC158188
0.9018	High Similarity	NPC173137
0.9018	High Similarity	NPC187354
0.9012	High Similarity	NPC476410
0.9012	High Similarity	NPC112380
0.9012	High Similarity	NPC172202
0.9012	High Similarity	NPC46736
0.9012	High Similarity	NPC210459
0.9012	High Similarity	NPC284127
0.9006	High Similarity	NPC35038
0.9006	High Similarity	NPC321916
0.9006	High Similarity	NPC309648
0.9006	High Similarity	NPC278778
0.9006	High Similarity	NPC150977
0.9006	High Similarity	NPC61112
0.9006	High Similarity	NPC291878
0.9006	High Similarity	NPC471500
0.9006	High Similarity	NPC198489
0.9006	High Similarity	NPC195796
0.9006	High Similarity	NPC3980
0.9	High Similarity	NPC121568
0.9	High Similarity	NPC185275
0.9	High Similarity	NPC298692
0.9	High Similarity	NPC268193
0.9	High Similarity	NPC244250
0.9	High Similarity	NPC74924
0.9	High Similarity	NPC20907
0.8994	High Similarity	NPC205046
0.8994	High Similarity	NPC59162
0.8994	High Similarity	NPC304295
0.8988	High Similarity	NPC98583
0.8982	High Similarity	NPC287884
0.8982	High Similarity	NPC8704
0.8982	High Similarity	NPC476365
0.8976	High Similarity	NPC476306
0.8976	High Similarity	NPC14662
0.8976	High Similarity	NPC470456
0.8976	High Similarity	NPC8965
0.897	High Similarity	NPC470457
0.897	High Similarity	NPC471788
0.897	High Similarity	NPC224280
0.897	High Similarity	NPC473010
0.8963	High Similarity	NPC211107
0.8963	High Similarity	NPC194427
0.896	High Similarity	NPC64755
0.896	High Similarity	NPC47905
0.896	High Similarity	NPC73929
0.896	High Similarity	NPC139683
0.8957	High Similarity	NPC475784
0.8957	High Similarity	NPC292863
0.8957	High Similarity	NPC476283
0.8957	High Similarity	NPC476280
0.8957	High Similarity	NPC36217
0.8957	High Similarity	NPC470183
0.8957	High Similarity	NPC184326
0.8957	High Similarity	NPC321399
0.8953	High Similarity	NPC318119
0.8951	High Similarity	NPC471515
0.8951	High Similarity	NPC237418
0.8951	High Similarity	NPC273843
0.8951	High Similarity	NPC1796
0.8951	High Similarity	NPC291508
0.8951	High Similarity	NPC183851
0.8951	High Similarity	NPC27337
0.8951	High Similarity	NPC472598
0.8951	High Similarity	NPC129684
0.8951	High Similarity	NPC474055
0.8951	High Similarity	NPC473272
0.8951	High Similarity	NPC257166
0.8951	High Similarity	NPC287789
0.8951	High Similarity	NPC271741
0.8951	High Similarity	NPC284820
0.8951	High Similarity	NPC471479
0.8951	High Similarity	NPC299520
0.8951	High Similarity	NPC183
0.8951	High Similarity	NPC63454
0.8944	High Similarity	NPC470327
0.8944	High Similarity	NPC67396
0.8944	High Similarity	NPC45849
0.8944	High Similarity	NPC200761
0.8944	High Similarity	NPC476169
0.8944	High Similarity	NPC477503
0.8944	High Similarity	NPC111341
0.8944	High Similarity	NPC304745
0.8941	High Similarity	NPC471789
0.8938	High Similarity	NPC260491
0.8938	High Similarity	NPC246162
0.8938	High Similarity	NPC9743
0.8938	High Similarity	NPC240476
0.8938	High Similarity	NPC36835
0.8938	High Similarity	NPC19721
0.8938	High Similarity	NPC61506
0.8935	High Similarity	NPC108202

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 NPC107627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	475
0.1-0.2	1003
0.2-0.3	1988
0.3-0.4	2625
0.4-0.5	1698
0.5-0.6	889
0.6-0.7	310
0.7-0.8	115
0.8-0.85	24
0.85-0.9	19
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9119	High Similarity	NPD2393	Clinical (unspecified phase)
0.882	High Similarity	NPD1934	Approved
0.8817	High Similarity	NPD7993	Clinical (unspecified phase)
0.8797	High Similarity	NPD1512	Approved
0.8788	High Similarity	NPD6959	Discontinued
0.8773	High Similarity	NPD4868	Clinical (unspecified phase)
0.8712	High Similarity	NPD8443	Clinical (unspecified phase)
0.8706	High Similarity	NPD6797	Phase 2
0.8696	High Similarity	NPD4380	Phase 2
0.8671	High Similarity	NPD1511	Approved
0.8655	High Similarity	NPD7251	Discontinued
0.865	High Similarity	NPD2801	Approved
0.8616	High Similarity	NPD4378	Clinical (unspecified phase)
0.8605	High Similarity	NPD4338	Clinical (unspecified phase)
0.8588	High Similarity	NPD7054	Approved
0.8545	High Similarity	NPD3882	Suspended
0.8538	High Similarity	NPD7472	Approved
0.8538	High Similarity	NPD7074	Phase 3
0.8529	High Similarity	NPD3818	Discontinued
0.8503	High Similarity	NPD5494	Approved
0.8497	Intermediate Similarity	NPD7808	Phase 3
0.8494	Intermediate Similarity	NPD7075	Discontinued
0.8485	Intermediate Similarity	NPD3817	Phase 2
0.848	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7411	Suspended
0.8294	Intermediate Similarity	NPD6232	Discontinued
0.8291	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6801	Discontinued
0.8239	Intermediate Similarity	NPD1549	Phase 2
0.8204	Intermediate Similarity	NPD7819	Suspended
0.8161	Intermediate Similarity	NPD5844	Phase 1
0.8155	Intermediate Similarity	NPD5402	Approved
0.8107	Intermediate Similarity	NPD7768	Phase 2
0.805	Intermediate Similarity	NPD1510	Phase 2
0.8034	Intermediate Similarity	NPD8313	Approved
0.8034	Intermediate Similarity	NPD8312	Approved
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2796	Approved
0.7988	Intermediate Similarity	NPD1465	Phase 2
0.7953	Intermediate Similarity	NPD3749	Approved
0.7952	Intermediate Similarity	NPD5403	Approved
0.7923	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6559	Discontinued
0.7879	Intermediate Similarity	NPD7390	Discontinued
0.7879	Intermediate Similarity	NPD6799	Approved
0.7874	Intermediate Similarity	NPD3787	Discontinued
0.7831	Intermediate Similarity	NPD5401	Approved
0.7831	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3926	Phase 2
0.7816	Intermediate Similarity	NPD1247	Approved
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7799	Intermediate Similarity	NPD943	Approved
0.7797	Intermediate Similarity	NPD3751	Discontinued
0.7747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD3750	Approved
0.7688	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1240	Approved
0.7688	Intermediate Similarity	NPD1613	Approved
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2800	Approved
0.7636	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6782	Approved
0.7632	Intermediate Similarity	NPD6778	Approved
0.7632	Intermediate Similarity	NPD6777	Approved
0.7632	Intermediate Similarity	NPD6776	Approved
0.7632	Intermediate Similarity	NPD6781	Approved
0.7632	Intermediate Similarity	NPD6779	Approved
0.7632	Intermediate Similarity	NPD6780	Approved
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD2533	Approved
0.7609	Intermediate Similarity	NPD8150	Discontinued
0.7607	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6234	Discontinued
0.7598	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD1607	Approved
0.7572	Intermediate Similarity	NPD8455	Phase 2
0.7566	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4908	Phase 1
0.7545	Intermediate Similarity	NPD6190	Approved
0.7544	Intermediate Similarity	NPD3226	Approved
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD8151	Discontinued
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.746	Intermediate Similarity	NPD4360	Phase 2
0.746	Intermediate Similarity	NPD4363	Phase 3
0.7455	Intermediate Similarity	NPD2935	Discontinued
0.7448	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD7698	Approved
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7423	Intermediate Similarity	NPD7697	Approved
0.7423	Intermediate Similarity	NPD7696	Phase 3
0.7414	Intermediate Similarity	NPD37	Approved
0.7412	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7394	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7378	Intermediate Similarity	NPD6651	Approved
0.7377	Intermediate Similarity	NPD5953	Discontinued
0.7368	Intermediate Similarity	NPD6535	Approved
0.7368	Intermediate Similarity	NPD6534	Approved
0.736	Intermediate Similarity	NPD7701	Phase 2
0.7349	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD6100	Approved
0.7349	Intermediate Similarity	NPD1551	Phase 2
0.7346	Intermediate Similarity	NPD2313	Discontinued
0.7337	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD7801	Approved
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7305	Intermediate Similarity	NPD2346	Discontinued
0.7305	Intermediate Similarity	NPD2344	Approved
0.7294	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7874	Approved
0.7286	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3027	Phase 3
0.7283	Intermediate Similarity	NPD1653	Approved
0.7278	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD7229	Phase 3
0.7268	Intermediate Similarity	NPD7286	Phase 2
0.7254	Intermediate Similarity	NPD7699	Phase 2
0.7254	Intermediate Similarity	NPD7700	Phase 2
0.725	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7783	Phase 2
0.7246	Intermediate Similarity	NPD5404	Approved
0.7246	Intermediate Similarity	NPD5406	Approved
0.7246	Intermediate Similarity	NPD5408	Approved
0.7246	Intermediate Similarity	NPD5405	Approved
0.7241	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1243	Approved
0.7215	Intermediate Similarity	NPD1610	Phase 2
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7194	Intermediate Similarity	NPD6823	Phase 2
0.7182	Intermediate Similarity	NPD5711	Approved
0.7182	Intermediate Similarity	NPD5710	Approved
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7240	Approved
0.7136	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD2309	Approved
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7108	Intermediate Similarity	NPD5124	Phase 1
0.7108	Intermediate Similarity	NPD447	Suspended
0.7108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7003	Approved
0.7076	Intermediate Similarity	NPD8166	Discontinued
0.7068	Intermediate Similarity	NPD4287	Approved
0.7062	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4361	Phase 2
0.7055	Intermediate Similarity	NPD2861	Phase 2
0.7048	Intermediate Similarity	NPD4060	Phase 1
0.7033	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD3268	Approved
0.7027	Intermediate Similarity	NPD7177	Discontinued
0.7022	Intermediate Similarity	NPD6844	Discontinued
0.7021	Intermediate Similarity	NPD7549	Discontinued
0.7019	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2403	Approved
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.6994	Remote Similarity	NPD2798	Approved
0.6988	Remote Similarity	NPD6233	Phase 2
0.6985	Remote Similarity	NPD4002	Approved
0.6985	Remote Similarity	NPD4004	Approved
0.6982	Remote Similarity	NPD7033	Discontinued
0.6971	Remote Similarity	NPD6273	Approved
0.697	Remote Similarity	NPD3450	Approved
0.697	Remote Similarity	NPD2494	Approved
0.697	Remote Similarity	NPD2493	Approved
0.697	Remote Similarity	NPD4625	Phase 3
0.697	Remote Similarity	NPD3452	Approved
0.6962	Remote Similarity	NPD1548	Phase 1
0.6959	Remote Similarity	NPD6213	Phase 3

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