NPASS Compound

Structure

CID11700 OpenBabel06191715342D 31 33 0 0 0 0 0 0 0 0999 V2000 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -1.8660 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 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 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 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 14 26 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 16 23 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 22 30 2 0 0 0 0 23 31 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	441.663
LogP:	5.847
LogD:	3.589
LogS:	-3.248
# Rotatable Bonds:	5
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	3.321
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	1.4902946531947237e-05
Pgp-inhibitor:	0.795
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.437

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	97.29582214355469%
Volume Distribution (VD):	0.802
Pgp-substrate:	5.337089538574219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.187
CYP2C19-inhibitor:	0.877
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.81
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.376
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	2.294
Half-life (T1/2):	0.555

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.7
Rat Oral Acute Toxicity:	0.26
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.727
Carcinogencity:	0.132
Eye Corrosion:	0.004
Eye Irritation:	0.897
Respiratory Toxicity:	0.229

Download Data

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

Natural Product: NPC11700

Natural Product ID:	NPC11700
*Common Name:**	Nigrasin I
IUPAC Name:	2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(2-methylbut-3-en-2-yl)-3-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	nigrasin I
Standard InCHIKey:	HNGMUJGQCGQWFH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-6-25(4,5)21-19(29)12-18(28)20-22(30)16(9-7-13(2)3)23(31-24(20)21)15-10-8-14(26)11-17(15)27/h6-8,10-12,26-29H,1,9H2,2-5H3
SMILES:	C=CC(C)(C)c1c(cc(c2c(=O)c(CC=C(C)C)c(c3ccc(cc3O)O)oc12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773619
PubChem CID:	52951053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003501] 3-prenylated flavones

*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
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[18330242]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	n.a.	twig	n.a.	PMID[21401118]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	twigs	Xinjiang Uygur Autonomous Region, China	2006-MAY	PMID[21401118]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	root bark	Konya, Turkey	2007-APR	PMID[24901948]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19738	Morus nigra	Species	Moraceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	250.63	%	PMID[568924]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	317.18	%	PMID[568924]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	179.84	%	PMID[568924]

☑ 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 NPC11700 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	420
0.1-0.2	1620
0.2-0.3	3818
0.3-0.4	10135
0.4-0.5	8400
0.5-0.6	3799
0.6-0.7	6007
0.7-0.8	4647
0.8-0.85	1879
0.85-0.9	1408
0.9-0.95	513
0.95-1	51

Similarity Score	Similarity Level	Natural Product ID
0.9708	High Similarity	NPC55018
0.9708	High Similarity	NPC96565
0.9708	High Similarity	NPC301217
0.9708	High Similarity	NPC216978
0.9708	High Similarity	NPC303633
0.9708	High Similarity	NPC220062
0.9645	High Similarity	NPC10990
0.9645	High Similarity	NPC300988
0.9638	High Similarity	NPC270883
0.9638	High Similarity	NPC241100
0.9638	High Similarity	NPC172986
0.9638	High Similarity	NPC261227
0.9638	High Similarity	NPC159275
0.9635	High Similarity	NPC201395
0.958	High Similarity	NPC476185
0.958	High Similarity	NPC321896
0.9571	High Similarity	NPC293053
0.9571	High Similarity	NPC212932
0.9571	High Similarity	NPC24821
0.9571	High Similarity	NPC9117
0.9571	High Similarity	NPC190637
0.9571	High Similarity	NPC219915
0.9568	High Similarity	NPC118840
0.9568	High Similarity	NPC110969
0.9568	High Similarity	NPC64908
0.9568	High Similarity	NPC282300
0.9568	High Similarity	NPC147688
0.9568	High Similarity	NPC205006
0.9568	High Similarity	NPC156590
0.9565	High Similarity	NPC18260
0.9565	High Similarity	NPC78913
0.9565	High Similarity	NPC217186
0.9565	High Similarity	NPC53181
0.951	High Similarity	NPC471114
0.9504	High Similarity	NPC234629
0.9504	High Similarity	NPC271288
0.9504	High Similarity	NPC476055
0.9504	High Similarity	NPC311741
0.9504	High Similarity	NPC273538
0.9504	High Similarity	NPC216538
0.9504	High Similarity	NPC326500
0.95	High Similarity	NPC11561
0.95	High Similarity	NPC226636
0.95	High Similarity	NPC214236
0.95	High Similarity	NPC299080
0.95	High Similarity	NPC200694
0.95	High Similarity	NPC62840
0.95	High Similarity	NPC473042
0.95	High Similarity	NPC78803
0.95	High Similarity	NPC293852
0.95	High Similarity	NPC59739
0.95	High Similarity	NPC144499
0.95	High Similarity	NPC217083
0.9496	High Similarity	NPC305355
0.9496	High Similarity	NPC11056
0.9496	High Similarity	NPC235239
0.9496	High Similarity	NPC475680
0.9496	High Similarity	NPC150522
0.9496	High Similarity	NPC69769
0.9489	High Similarity	NPC13408
0.9444	High Similarity	NPC188403
0.9437	High Similarity	NPC306488
0.9437	High Similarity	NPC154217
0.9437	High Similarity	NPC477955
0.9437	High Similarity	NPC178343
0.9437	High Similarity	NPC5820
0.9437	High Similarity	NPC124729
0.9433	High Similarity	NPC166138
0.9433	High Similarity	NPC38219
0.9433	High Similarity	NPC106985
0.9433	High Similarity	NPC18585
0.9429	High Similarity	NPC14871
0.9429	High Similarity	NPC103362
0.942	High Similarity	NPC228661
0.9379	High Similarity	NPC305965
0.9375	High Similarity	NPC10027
0.9375	High Similarity	NPC65775
0.9371	High Similarity	NPC237635
0.9371	High Similarity	NPC14001
0.9371	High Similarity	NPC79469
0.9371	High Similarity	NPC296998
0.9371	High Similarity	NPC166757
0.9371	High Similarity	NPC473077
0.9371	High Similarity	NPC104406
0.9371	High Similarity	NPC24673
0.9371	High Similarity	NPC201731
0.9371	High Similarity	NPC97716
0.9371	High Similarity	NPC308200
0.9366	High Similarity	NPC470674
0.9366	High Similarity	NPC319752
0.9366	High Similarity	NPC470673
0.9366	High Similarity	NPC196137
0.9366	High Similarity	NPC1886
0.9366	High Similarity	NPC117716
0.9366	High Similarity	NPC224714
0.9362	High Similarity	NPC161506
0.9362	High Similarity	NPC227579
0.9362	High Similarity	NPC324436
0.9362	High Similarity	NPC177354
0.9362	High Similarity	NPC32739
0.9362	High Similarity	NPC66515
0.9362	High Similarity	NPC328164
0.9362	High Similarity	NPC36181
0.9362	High Similarity	NPC194432
0.9362	High Similarity	NPC306829
0.9362	High Similarity	NPC148757
0.9362	High Similarity	NPC125855
0.9362	High Similarity	NPC296917
0.9362	High Similarity	NPC324134
0.9362	High Similarity	NPC182852
0.9362	High Similarity	NPC220998
0.9362	High Similarity	NPC228504
0.9362	High Similarity	NPC64915
0.9362	High Similarity	NPC167624
0.9362	High Similarity	NPC107572
0.9362	High Similarity	NPC10937
0.9362	High Similarity	NPC40833
0.9362	High Similarity	NPC37496
0.9362	High Similarity	NPC76338
0.9362	High Similarity	NPC223500
0.9362	High Similarity	NPC265040
0.9362	High Similarity	NPC1089
0.9362	High Similarity	NPC78
0.9362	High Similarity	NPC166482
0.9362	High Similarity	NPC166934
0.9362	High Similarity	NPC76372
0.9357	High Similarity	NPC48624
0.9357	High Similarity	NPC215311
0.9357	High Similarity	NPC172250
0.9357	High Similarity	NPC144118
0.9357	High Similarity	NPC259166
0.9357	High Similarity	NPC219917
0.9357	High Similarity	NPC326109
0.9357	High Similarity	NPC80962
0.9357	High Similarity	NPC213659
0.9357	High Similarity	NPC204985
0.9353	High Similarity	NPC470669
0.9353	High Similarity	NPC131130
0.9353	High Similarity	NPC470668
0.9348	High Similarity	NPC29353
0.9348	High Similarity	NPC124784
0.9348	High Similarity	NPC47815
0.9348	High Similarity	NPC194281
0.9348	High Similarity	NPC174999
0.9348	High Similarity	NPC473887
0.9348	High Similarity	NPC127447
0.9348	High Similarity	NPC231772
0.9348	High Similarity	NPC234133
0.931	High Similarity	NPC471115
0.931	High Similarity	NPC29777
0.9306	High Similarity	NPC145467
0.9306	High Similarity	NPC168085
0.9306	High Similarity	NPC39195
0.9306	High Similarity	NPC6511
0.9306	High Similarity	NPC266572
0.9306	High Similarity	NPC244407
0.9306	High Similarity	NPC296869
0.9301	High Similarity	NPC111786
0.9301	High Similarity	NPC20488
0.9301	High Similarity	NPC472629
0.9301	High Similarity	NPC181388
0.9301	High Similarity	NPC470322
0.9301	High Similarity	NPC176229
0.9301	High Similarity	NPC476088
0.9301	High Similarity	NPC267375
0.9301	High Similarity	NPC88964
0.9301	High Similarity	NPC214774
0.9301	High Similarity	NPC470647
0.9301	High Similarity	NPC220418
0.9301	High Similarity	NPC142405
0.9301	High Similarity	NPC54577
0.9301	High Similarity	NPC312973
0.9301	High Similarity	NPC475052
0.9301	High Similarity	NPC474161
0.9301	High Similarity	NPC83357
0.9301	High Similarity	NPC67805
0.9301	High Similarity	NPC246948
0.9301	High Similarity	NPC301276
0.9301	High Similarity	NPC195621
0.9296	High Similarity	NPC143896
0.9296	High Similarity	NPC39329
0.9296	High Similarity	NPC149026
0.9296	High Similarity	NPC112791
0.9296	High Similarity	NPC91560
0.9296	High Similarity	NPC310130
0.9296	High Similarity	NPC278249
0.9296	High Similarity	NPC150408
0.9296	High Similarity	NPC196459
0.9296	High Similarity	NPC478086
0.9296	High Similarity	NPC188632
0.9296	High Similarity	NPC87609
0.9296	High Similarity	NPC221432
0.9296	High Similarity	NPC158874
0.9296	High Similarity	NPC68104
0.9296	High Similarity	NPC94794
0.9296	High Similarity	NPC185276
0.9296	High Similarity	NPC75049
0.9296	High Similarity	NPC107177
0.9296	High Similarity	NPC164980
0.9296	High Similarity	NPC81697

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 NPC11700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	951
0.2-0.3	1456
0.3-0.4	2600
0.4-0.5	2027
0.5-0.6	1147
0.6-0.7	401
0.7-0.8	125
0.8-0.85	37
0.85-0.9	26
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9504	High Similarity	NPD4378	Clinical (unspecified phase)
0.9231	High Similarity	NPD7410	Clinical (unspecified phase)
0.9007	High Similarity	NPD1550	Clinical (unspecified phase)
0.9007	High Similarity	NPD1552	Clinical (unspecified phase)
0.9	High Similarity	NPD1510	Phase 2
0.8944	High Similarity	NPD1549	Phase 2
0.8936	High Similarity	NPD2796	Approved
0.8933	High Similarity	NPD8443	Clinical (unspecified phase)
0.8881	High Similarity	NPD2800	Approved
0.8867	High Similarity	NPD2393	Clinical (unspecified phase)
0.8849	High Similarity	NPD1240	Approved
0.8792	High Similarity	NPD4380	Phase 2
0.8767	High Similarity	NPD1511	Approved
0.8742	High Similarity	NPD7819	Suspended
0.8733	High Similarity	NPD7411	Suspended
0.8723	High Similarity	NPD1607	Approved
0.8693	High Similarity	NPD7075	Discontinued
0.869	High Similarity	NPD3750	Approved
0.8649	High Similarity	NPD1512	Approved
0.8618	High Similarity	NPD7096	Clinical (unspecified phase)
0.8618	High Similarity	NPD2801	Approved
0.8553	High Similarity	NPD1934	Approved
0.8553	High Similarity	NPD6801	Discontinued
0.8543	High Similarity	NPD6599	Discontinued
0.8506	High Similarity	NPD7768	Phase 2
0.8481	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6651	Approved
0.8452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8389	Intermediate Similarity	NPD6799	Approved
0.8367	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1243	Approved
0.8345	Intermediate Similarity	NPD3748	Approved
0.8345	Intermediate Similarity	NPD2799	Discontinued
0.8333	Intermediate Similarity	NPD3749	Approved
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD6100	Approved
0.8288	Intermediate Similarity	NPD6099	Approved
0.8269	Intermediate Similarity	NPD3882	Suspended
0.8232	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2344	Approved
0.8205	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2313	Discontinued
0.8163	Intermediate Similarity	NPD2935	Discontinued
0.8163	Intermediate Similarity	NPD1551	Phase 2
0.8137	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6166	Phase 2
0.8125	Intermediate Similarity	NPD6232	Discontinued
0.8113	Intermediate Similarity	NPD5494	Approved
0.8105	Intermediate Similarity	NPD920	Approved
0.8095	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2534	Approved
0.8092	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD2532	Approved
0.8086	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD4628	Phase 3
0.8067	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD3268	Approved
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8028	Intermediate Similarity	NPD2798	Approved
0.8013	Intermediate Similarity	NPD2309	Approved
0.8	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD3226	Approved
0.7988	Intermediate Similarity	NPD7054	Approved
0.7987	Intermediate Similarity	NPD5403	Approved
0.7974	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1203	Approved
0.7958	Intermediate Similarity	NPD2797	Approved
0.7947	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7939	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD4908	Phase 1
0.7908	Intermediate Similarity	NPD7390	Discontinued
0.7892	Intermediate Similarity	NPD6797	Phase 2
0.7879	Intermediate Similarity	NPD7286	Phase 2
0.7867	Intermediate Similarity	NPD2346	Discontinued
0.7857	Intermediate Similarity	NPD5401	Approved
0.7844	Intermediate Similarity	NPD6559	Discontinued
0.7844	Intermediate Similarity	NPD7251	Discontinued
0.7823	Intermediate Similarity	NPD943	Approved
0.7812	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD422	Phase 1
0.7801	Intermediate Similarity	NPD1610	Phase 2
0.7798	Intermediate Similarity	NPD7808	Phase 3
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.777	Intermediate Similarity	NPD1548	Phase 1
0.7759	Intermediate Similarity	NPD4360	Phase 2
0.7759	Intermediate Similarity	NPD4363	Phase 3
0.775	Intermediate Similarity	NPD5402	Approved
0.7746	Intermediate Similarity	NPD3972	Approved
0.7746	Intermediate Similarity	NPD9717	Approved
0.774	Intermediate Similarity	NPD4625	Phase 3
0.7733	Intermediate Similarity	NPD4308	Phase 3
0.7733	Intermediate Similarity	NPD7033	Discontinued
0.7716	Intermediate Similarity	NPD919	Approved
0.7714	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD4361	Phase 2
0.7708	Intermediate Similarity	NPD3267	Approved
0.7708	Intermediate Similarity	NPD3266	Approved
0.7692	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6832	Phase 2
0.7658	Intermediate Similarity	NPD7458	Discontinued
0.764	Intermediate Similarity	NPD4288	Approved
0.7639	Intermediate Similarity	NPD3225	Approved
0.7636	Intermediate Similarity	NPD3926	Phase 2
0.7628	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1608	Approved
0.7622	Intermediate Similarity	NPD1247	Approved
0.7597	Intermediate Similarity	NPD7003	Approved
0.7578	Intermediate Similarity	NPD1465	Phase 2
0.7552	Intermediate Similarity	NPD1201	Approved
0.7533	Intermediate Similarity	NPD5124	Phase 1
0.7533	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2654	Approved
0.7472	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5710	Approved
0.747	Intermediate Similarity	NPD5711	Approved
0.7467	Intermediate Similarity	NPD4307	Phase 2
0.7466	Intermediate Similarity	NPD1164	Approved
0.7466	Intermediate Similarity	NPD1470	Approved
0.7465	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5408	Approved
0.7451	Intermediate Similarity	NPD5406	Approved
0.7451	Intermediate Similarity	NPD5404	Approved
0.7451	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD3764	Approved
0.745	Intermediate Similarity	NPD1296	Phase 2
0.745	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4749	Approved
0.7432	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2296	Approved
0.7421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD17	Approved
0.7412	Intermediate Similarity	NPD1729	Discontinued
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7368	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7229	Phase 3
0.7365	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD411	Approved
0.733	Intermediate Similarity	NPD4287	Approved
0.7329	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6104	Discontinued
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1933	Approved
0.7303	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6585	Discontinued
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9545	Approved
0.7256	Intermediate Similarity	NPD5761	Phase 2
0.7256	Intermediate Similarity	NPD5760	Phase 2
0.7254	Intermediate Similarity	NPD9493	Approved
0.725	Intermediate Similarity	NPD6273	Approved
0.7247	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5890	Approved
0.7239	Intermediate Similarity	NPD5889	Approved
0.7237	Intermediate Similarity	NPD1613	Approved
0.7237	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4476	Approved
0.7226	Intermediate Similarity	NPD4477	Approved
0.7219	Intermediate Similarity	NPD6798	Discontinued
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7204	Intermediate Similarity	NPD7584	Approved
0.7202	Intermediate Similarity	NPD7199	Phase 2
0.7193	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD230	Phase 1
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7176	Intermediate Similarity	NPD2403	Approved
0.7163	Intermediate Similarity	NPD1241	Discontinued
0.7162	Intermediate Similarity	NPD1876	Approved
0.7162	Intermediate Similarity	NPD8651	Approved
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD8313	Approved
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7126	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4060	Phase 1
0.7118	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2354	Approved
0.7103	Intermediate Similarity	NPD1651	Approved
0.7093	Intermediate Similarity	NPD3751	Discontinued
0.7093	Intermediate Similarity	NPD7177	Discontinued
0.7093	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6279	Approved
0.7091	Intermediate Similarity	NPD6280	Approved
0.7091	Intermediate Similarity	NPD6844	Discontinued
0.7086	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7447	Phase 1
0.7076	Intermediate Similarity	NPD7784	Clinical (unspecified phase)

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