NPASS Compound

Structure

CID107244 OpenBabel06191715452D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 -0.0000 -2.0000 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 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -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 -0.0000 3.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 3 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 -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 -0.5000 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -3.5491 -0.1910 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 1 9 2 0 0 0 0 2 9 1 0 0 0 0 3 20 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 15 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	280.771
LogP:	0.393
LogD:	0.571
LogS:	-2.277
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	4.572
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.336
MDCK Permeability:	2.1019681298639625e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.144
20% Bioavailability (F20%):	0.773
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	83.95677947998047%
Volume Distribution (VD):	0.327
Pgp-substrate:	19.860347747802734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	2.562
Half-life (T1/2):	0.695

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.099
Skin Sensitization:	0.387
Carcinogencity:	0.243
Eye Corrosion:	0.454
Eye Irritation:	0.932
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC107244

Natural Product ID:	NPC107244
*Common Name:**	9-(2-Hydroxy-3-Methylbut-3-Enoxy)-4-Methoxyfuro[3,2-G]Chromen-7-One
IUPAC Name:	9-(2-hydroxy-3-methylbut-3-enoxy)-4-methoxyfuro[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	UBAMGTKSOKGECF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-9(2)12(18)8-22-17-15-11(6-7-21-15)14(20-3)10-4-5-13(19)23-16(10)17/h4-7,12,18H,1,8H2,2-3H3
SMILES:	COc1c2ccoc2c(c2c1ccc(=O)o2)OCC(C(=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1699927
PubChem CID:	616064
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens [CHEMONTID:0002832] 5-methoxypsoralens

*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
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	bought from a drugstore in Beijing	n.a.	PMID[10514305]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[14738377]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	n.a.	n.a.	PMID[21524582]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10385	Ptelea trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10385	Ptelea trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30713	Angelica talwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10385	Ptelea trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10385	Ptelea trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	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
Potency	7

Activity Type	# Activity
Individual Protein	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29081.0	nM	PMID[512225]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[512225]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	6309.6	nM	PMID[512225]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[512225]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	125892.5	nM	PMID[512225]
NPT2	Others	Unspecified		Potency	n.a.	92.0	nM	PMID[512225]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[512225]

☑ 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 NPC107244 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	406
0.1-0.2	1773
0.2-0.3	4562
0.3-0.4	9786
0.4-0.5	8393
0.5-0.6	4107
0.6-0.7	5645
0.7-0.8	5039
0.8-0.85	2070
0.85-0.9	852
0.9-0.95	52
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC224165
0.9697	High Similarity	NPC53917
0.9636	High Similarity	NPC233956
0.9634	High Similarity	NPC51404
0.9571	High Similarity	NPC193881
0.9571	High Similarity	NPC155264
0.9571	High Similarity	NPC210460
0.9571	High Similarity	NPC67450
0.9515	High Similarity	NPC281835
0.9448	High Similarity	NPC179464
0.9398	High Similarity	NPC144288
0.9387	High Similarity	NPC78612
0.9387	High Similarity	NPC234536
0.9325	High Similarity	NPC216092
0.9264	High Similarity	NPC169
0.9264	High Similarity	NPC243509
0.9249	High Similarity	NPC73703
0.9212	High Similarity	NPC15819
0.9207	High Similarity	NPC14822
0.9202	High Similarity	NPC33320
0.9157	High Similarity	NPC173149
0.9157	High Similarity	NPC179015
0.9146	High Similarity	NPC95472
0.9146	High Similarity	NPC303210
0.9146	High Similarity	NPC239270
0.9146	High Similarity	NPC49009
0.9141	High Similarity	NPC269495
0.9091	High Similarity	NPC264293
0.9048	High Similarity	NPC247973
0.9042	High Similarity	NPC36320
0.8929	High Similarity	NPC470457
0.8929	High Similarity	NPC45449
0.8922	High Similarity	NPC272722
0.8922	High Similarity	NPC81679
0.8889	High Similarity	NPC121333
0.8882	High Similarity	NPC152477
0.8869	High Similarity	NPC1755
0.8869	High Similarity	NPC1706
0.8869	High Similarity	NPC470459
0.8869	High Similarity	NPC59295
0.8869	High Similarity	NPC65846
0.8869	High Similarity	NPC263092
0.8869	High Similarity	NPC39305
0.8855	High Similarity	NPC195832
0.8844	High Similarity	NPC8127
0.8844	High Similarity	NPC49667
0.8837	High Similarity	NPC65885
0.8837	High Similarity	NPC72455
0.8837	High Similarity	NPC310794
0.8837	High Similarity	NPC261471
0.883	High Similarity	NPC131866
0.8824	High Similarity	NPC186392
0.8824	High Similarity	NPC241820
0.8824	High Similarity	NPC470456
0.8824	High Similarity	NPC158761
0.881	High Similarity	NPC312056
0.881	High Similarity	NPC238995
0.881	High Similarity	NPC84515
0.8802	High Similarity	NPC246478
0.8793	High Similarity	NPC297807
0.8793	High Similarity	NPC98546
0.8786	High Similarity	NPC287243
0.8773	High Similarity	NPC191104
0.8772	High Similarity	NPC280493
0.8772	High Similarity	NPC242395
0.8765	High Similarity	NPC470462
0.8765	High Similarity	NPC323137
0.8765	High Similarity	NPC277480
0.8765	High Similarity	NPC128293
0.8757	High Similarity	NPC472582
0.8757	High Similarity	NPC124038
0.875	High Similarity	NPC308992
0.875	High Similarity	NPC188486
0.8743	High Similarity	NPC16935
0.8743	High Similarity	NPC196879
0.8743	High Similarity	NPC104682
0.8736	High Similarity	NPC164384
0.8736	High Similarity	NPC156635
0.8735	High Similarity	NPC45131
0.8735	High Similarity	NPC19860
0.8728	High Similarity	NPC82217
0.8728	High Similarity	NPC216842
0.8728	High Similarity	NPC476640
0.8727	High Similarity	NPC186507
0.8721	High Similarity	NPC28042
0.8721	High Similarity	NPC476641
0.8721	High Similarity	NPC78830
0.8721	High Similarity	NPC218533
0.872	High Similarity	NPC98028
0.8713	High Similarity	NPC8965
0.8712	High Similarity	NPC88445
0.8706	High Similarity	NPC329215
0.8706	High Similarity	NPC37183
0.8706	High Similarity	NPC204088
0.8706	High Similarity	NPC38914
0.8706	High Similarity	NPC259007
0.8706	High Similarity	NPC291110
0.8698	High Similarity	NPC193998
0.8698	High Similarity	NPC471745
0.869	High Similarity	NPC263449
0.869	High Similarity	NPC287328
0.869	High Similarity	NPC328102
0.869	High Similarity	NPC282009
0.869	High Similarity	NPC476980
0.8686	High Similarity	NPC67302
0.8686	High Similarity	NPC168584
0.8683	High Similarity	NPC203891
0.8683	High Similarity	NPC470402
0.8683	High Similarity	NPC101830
0.8683	High Similarity	NPC110070
0.8683	High Similarity	NPC270044
0.8683	High Similarity	NPC19097
0.8683	High Similarity	NPC476981
0.8678	High Similarity	NPC289244
0.8678	High Similarity	NPC264735
0.8675	High Similarity	NPC189960
0.8675	High Similarity	NPC34725
0.8675	High Similarity	NPC250769
0.8675	High Similarity	NPC241774
0.8675	High Similarity	NPC122623
0.8675	High Similarity	NPC32557
0.8675	High Similarity	NPC276059
0.8675	High Similarity	NPC295608
0.8675	High Similarity	NPC278010
0.8671	High Similarity	NPC230619
0.8671	High Similarity	NPC247964
0.8671	High Similarity	NPC54098
0.8671	High Similarity	NPC157522
0.8667	High Similarity	NPC60211
0.8667	High Similarity	NPC60848
0.8663	High Similarity	NPC247136
0.8663	High Similarity	NPC211309
0.8659	High Similarity	NPC155882
0.8655	High Similarity	NPC13481
0.8655	High Similarity	NPC119589
0.8655	High Similarity	NPC207575
0.8655	High Similarity	NPC173292
0.8647	High Similarity	NPC472625
0.8647	High Similarity	NPC234004
0.8647	High Similarity	NPC133065
0.8644	High Similarity	NPC228209
0.8644	High Similarity	NPC8927
0.8639	High Similarity	NPC349525
0.8639	High Similarity	NPC471499
0.8639	High Similarity	NPC473106
0.8639	High Similarity	NPC45124
0.8639	High Similarity	NPC30655
0.8639	High Similarity	NPC74854
0.8639	High Similarity	NPC112418
0.8639	High Similarity	NPC258331
0.8639	High Similarity	NPC103201
0.8631	High Similarity	NPC253634
0.8631	High Similarity	NPC95936
0.8631	High Similarity	NPC193842
0.8631	High Similarity	NPC25495
0.8631	High Similarity	NPC105242
0.8631	High Similarity	NPC22192
0.8631	High Similarity	NPC261004
0.8631	High Similarity	NPC250214
0.8631	High Similarity	NPC83763
0.8631	High Similarity	NPC130894
0.8631	High Similarity	NPC18772
0.8631	High Similarity	NPC300943
0.8631	High Similarity	NPC4481
0.8631	High Similarity	NPC168616
0.8631	High Similarity	NPC176300
0.8631	High Similarity	NPC22472
0.8631	High Similarity	NPC9609
0.8631	High Similarity	NPC191459
0.8631	High Similarity	NPC152904
0.8631	High Similarity	NPC152166
0.8631	High Similarity	NPC19687
0.8631	High Similarity	NPC204854
0.8631	High Similarity	NPC250076
0.8631	High Similarity	NPC143828
0.8631	High Similarity	NPC7846
0.8631	High Similarity	NPC18607
0.8631	High Similarity	NPC288669
0.8631	High Similarity	NPC115798
0.8629	High Similarity	NPC472382
0.8629	High Similarity	NPC198324
0.8629	High Similarity	NPC472380
0.8629	High Similarity	NPC325176
0.8629	High Similarity	NPC472384
0.8629	High Similarity	NPC472385
0.8623	High Similarity	NPC317383
0.8623	High Similarity	NPC303255
0.8623	High Similarity	NPC49824
0.8623	High Similarity	NPC266960
0.8623	High Similarity	NPC245546
0.8623	High Similarity	NPC472461
0.8623	High Similarity	NPC43243
0.8623	High Similarity	NPC265511
0.8623	High Similarity	NPC257277
0.8623	High Similarity	NPC292107
0.8623	High Similarity	NPC178854
0.8621	High Similarity	NPC277510
0.8621	High Similarity	NPC37606
0.8621	High Similarity	NPC181523
0.8621	High Similarity	NPC62640

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 NPC107244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	950
0.2-0.3	2066
0.3-0.4	2632
0.4-0.5	1763
0.5-0.6	914
0.6-0.7	303
0.7-0.8	105
0.8-0.85	32
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9202	High Similarity	NPD919	Approved
0.9091	High Similarity	NPD1247	Approved
0.8735	High Similarity	NPD3882	Suspended
0.8675	High Similarity	NPD3817	Phase 2
0.8589	High Similarity	NPD920	Approved
0.8571	High Similarity	NPD4338	Clinical (unspecified phase)
0.8554	High Similarity	NPD6801	Discontinued
0.8503	High Similarity	NPD7096	Clinical (unspecified phase)
0.8503	High Similarity	NPD2801	Approved
0.8497	Intermediate Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD5494	Approved
0.8466	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD5402	Approved
0.8448	Intermediate Similarity	NPD5844	Phase 1
0.8409	Intermediate Similarity	NPD6559	Discontinued
0.8393	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1934	Approved
0.8293	Intermediate Similarity	NPD6799	Approved
0.8276	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6166	Phase 2
0.816	Intermediate Similarity	NPD1243	Approved
0.8156	Intermediate Similarity	NPD7808	Phase 3
0.8146	Intermediate Similarity	NPD6797	Phase 2
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD3926	Phase 2
0.8107	Intermediate Similarity	NPD4380	Phase 2
0.8107	Intermediate Similarity	NPD6599	Discontinued
0.8101	Intermediate Similarity	NPD7251	Discontinued
0.8084	Intermediate Similarity	NPD1512	Approved
0.8081	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6232	Discontinued
0.8036	Intermediate Similarity	NPD5403	Approved
0.8034	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7054	Approved
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.7989	Intermediate Similarity	NPD7472	Approved
0.7989	Intermediate Similarity	NPD7074	Phase 3
0.7978	Intermediate Similarity	NPD8434	Phase 2
0.7965	Intermediate Similarity	NPD7819	Suspended
0.7964	Intermediate Similarity	NPD1511	Approved
0.7944	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5401	Approved
0.7849	Intermediate Similarity	NPD7411	Suspended
0.7829	Intermediate Similarity	NPD3749	Approved
0.7811	Intermediate Similarity	NPD2533	Approved
0.7811	Intermediate Similarity	NPD2532	Approved
0.7811	Intermediate Similarity	NPD2534	Approved
0.7759	Intermediate Similarity	NPD1465	Phase 2
0.7758	Intermediate Similarity	NPD2796	Approved
0.7758	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD447	Suspended
0.7713	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1549	Phase 2
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1510	Phase 2
0.7582	Intermediate Similarity	NPD3751	Discontinued
0.7574	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD1653	Approved
0.7571	Intermediate Similarity	NPD7768	Phase 2
0.7569	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1551	Phase 2
0.754	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6190	Approved
0.7515	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD230	Phase 1
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD6959	Discontinued
0.7472	Intermediate Similarity	NPD4965	Approved
0.7472	Intermediate Similarity	NPD4967	Phase 2
0.7472	Intermediate Similarity	NPD4966	Approved
0.7471	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3787	Discontinued
0.7455	Intermediate Similarity	NPD1240	Approved
0.7429	Intermediate Similarity	NPD3226	Approved
0.7396	Intermediate Similarity	NPD2344	Approved
0.7391	Intermediate Similarity	NPD2163	Approved
0.7389	Intermediate Similarity	NPD6234	Discontinued
0.7381	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD3750	Approved
0.7366	Intermediate Similarity	NPD5953	Discontinued
0.7365	Intermediate Similarity	NPD1607	Approved
0.7351	Intermediate Similarity	NPD7286	Phase 2
0.7349	Intermediate Similarity	NPD943	Approved
0.7341	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2313	Discontinued
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7435	Discontinued
0.7293	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5710	Approved
0.7268	Intermediate Similarity	NPD5711	Approved
0.7225	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD8150	Discontinued
0.7204	Intermediate Similarity	NPD7228	Approved
0.7204	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6355	Discontinued
0.7196	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD6233	Phase 2
0.7176	Intermediate Similarity	NPD3748	Approved
0.7176	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7033	Discontinued
0.7174	Intermediate Similarity	NPD7229	Phase 3
0.7172	Intermediate Similarity	NPD6782	Approved
0.7172	Intermediate Similarity	NPD6779	Approved
0.7172	Intermediate Similarity	NPD6776	Approved
0.7172	Intermediate Similarity	NPD6778	Approved
0.7172	Intermediate Similarity	NPD6781	Approved
0.7172	Intermediate Similarity	NPD6777	Approved
0.7172	Intermediate Similarity	NPD6780	Approved
0.7169	Intermediate Similarity	NPD3027	Phase 3
0.7158	Intermediate Similarity	NPD8313	Approved
0.7158	Intermediate Similarity	NPD8312	Approved
0.7152	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD5242	Approved
0.7127	Intermediate Similarity	NPD5353	Approved
0.7126	Intermediate Similarity	NPD6798	Discontinued
0.7108	Intermediate Similarity	NPD6832	Phase 2
0.7108	Intermediate Similarity	NPD7874	Approved
0.7108	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5124	Phase 1
0.7101	Intermediate Similarity	NPD1933	Approved
0.7101	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2403	Approved
0.7095	Intermediate Similarity	NPD7907	Approved
0.7093	Intermediate Similarity	NPD1471	Phase 3
0.7085	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4665	Approved
0.7081	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD7783	Phase 2
0.7073	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5761	Phase 2
0.7072	Intermediate Similarity	NPD5760	Phase 2
0.7059	Intermediate Similarity	NPD8151	Discontinued
0.7055	Intermediate Similarity	NPD9717	Approved
0.7053	Intermediate Similarity	NPD6765	Approved
0.7053	Intermediate Similarity	NPD6764	Approved
0.7041	Intermediate Similarity	NPD4060	Phase 1
0.7039	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1203	Approved
0.7028	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7024	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3057	Approved
0.7011	Intermediate Similarity	NPD1652	Phase 2
0.7005	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6808	Phase 2
0.6986	Remote Similarity	NPD8404	Phase 2
0.698	Remote Similarity	NPD7698	Approved
0.698	Remote Similarity	NPD7697	Approved
0.698	Remote Similarity	NPD7696	Phase 3
0.6974	Remote Similarity	NPD4287	Approved
0.6971	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5049	Phase 3
0.6963	Remote Similarity	NPD7240	Approved
0.6961	Remote Similarity	NPD6386	Approved
0.6961	Remote Similarity	NPD6385	Approved
0.6961	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6651	Approved
0.6954	Remote Similarity	NPD2424	Discontinued
0.6946	Remote Similarity	NPD7870	Phase 2
0.6946	Remote Similarity	NPD7871	Phase 2
0.6932	Remote Similarity	NPD3887	Approved
0.6932	Remote Similarity	NPD2354	Approved
0.6931	Remote Similarity	NPD3533	Approved
0.6931	Remote Similarity	NPD2972	Approved
0.6927	Remote Similarity	NPD7701	Phase 2
0.6927	Remote Similarity	NPD7549	Discontinued
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD6844	Discontinued
0.6923	Remote Similarity	NPD411	Approved
0.6919	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD6535	Approved
0.6915	Remote Similarity	NPD4107	Approved
0.6907	Remote Similarity	NPD6784	Approved
0.6907	Remote Similarity	NPD6785	Approved
0.6905	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6004	Phase 3
0.6897	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6005	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