NPASS Compound

Structure

CID49667 OpenBabel06191715382D 31 34 0 0 0 0 0 0 0 0999 V2000 6.7712 -2.9334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6179 -1.4677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6705 -2.9330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8474 1.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9251 -1.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9254 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3866 0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2331 1.4650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2326 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -1.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5397 -1.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7714 -1.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3864 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0791 -0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5399 -0.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8466 -1.4664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0793 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5398 -1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5396 -0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 -0.4885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 -1.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6937 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8467 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9258 1.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4086 -1.9674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4082 0.0135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6932 -2.9329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6937 0.9770 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 6 1 0 0 0 0 5 13 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 10 19 2 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 14 16 1 0 0 0 0 15 18 2 0 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 31 1 0 0 0 0 22 23 2 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.16
Volume:	433.107
LogP:	5.952
LogD:	3.914
LogS:	-3.703
# Rotatable Bonds:	5
TPSA:	92.29
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	2.865
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.087
MDCK Permeability:	1.1752193131542299e-05
Pgp-inhibitor:	0.394
Pgp-substrate:	0.076
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.313

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	88.60990142822266%
Volume Distribution (VD):	0.596
Pgp-substrate:	11.969287872314453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.81
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.337
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	13.447
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.623
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.591
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.917
Carcinogencity:	0.126
Eye Corrosion:	0.003
Eye Irritation:	0.892
Respiratory Toxicity:	0.473

Download Data

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

Natural Product: NPC49667

Natural Product ID:	NPC49667
*Common Name:**	Prenylcandidusin A
IUPAC Name:	7-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-6,9-dimethoxydibenzofuran-2,3-diol
Synonyms:	Prenylcandidusin A
Standard InCHIKey:	BNLTUQWJGCSQHG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O6/c1-13(2)5-6-15-9-14(7-8-18(15)26)16-11-22(29-3)23-17-10-19(27)20(28)12-21(17)31-25(23)24(16)30-4/h5,7-12,26-28H,6H2,1-4H3
SMILES:	CC(=CCc1cc(ccc1O)c1cc(c2c3cc(c(cc3oc2c1OC)O)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795461
PubChem CID:	53354806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0002584] Phenylbenzofurans

*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
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21486068]
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	a root soil fungus isolated from the mangrove plant Acrostichum aureum	n.a.	n.a.	PMID[21486068]
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	isolated from the root soil of the mangrove plant Acrostichum aureum	n.a.	n.a.	PMID[21486068]
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21899268]
NPO13765	Acrostichum aureum	Species	Pteridaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22906240]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12872	Taraxacum disseminatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12686	Sideritis hirsuta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22797	Fleroya stipulosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9892	Aspergillus taichungensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13272	Ulva lactuca	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7010	Anthocleista procera	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14461	Vibrio fluvialis	Species	Vibrionaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13868	Gnaphalium oligandrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11049	Solanum capsicastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10556	Eria jarensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11828	Mucor hiemalis	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14357	Ixeris denticulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26896	Wulfenia orientalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13765	Acrostichum aureum	Species	Pteridaceae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11830.0	nM	PMID[507410]
NPT168	Cell Line	P388	Mus musculus	IC50	=	16500.0	nM	PMID[507410]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	53200.0	nM	PMID[507410]

☑ 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 NPC49667 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	461
0.1-0.2	2006
0.2-0.3	4584
0.3-0.4	11220
0.4-0.5	6606
0.5-0.6	3773
0.6-0.7	5284
0.7-0.8	5250
0.8-0.85	2014
0.85-0.9	1141
0.9-0.95	340
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC8127
0.9877	High Similarity	NPC82217
0.9877	High Similarity	NPC216842
0.9877	High Similarity	NPC476640
0.9877	High Similarity	NPC65885
0.9817	High Similarity	NPC287243
0.9816	High Similarity	NPC54098
0.9816	High Similarity	NPC230619
0.9755	High Similarity	NPC476641
0.9632	High Similarity	NPC470704
0.9512	High Similarity	NPC50394
0.9509	High Similarity	NPC45449
0.9509	High Similarity	NPC36320
0.9464	High Similarity	NPC297807
0.9464	High Similarity	NPC98546
0.9448	High Similarity	NPC1755
0.9448	High Similarity	NPC1706
0.9448	High Similarity	NPC39305
0.9448	High Similarity	NPC263092
0.9448	High Similarity	NPC59295
0.9394	High Similarity	NPC247973
0.9387	High Similarity	NPC84515
0.9387	High Similarity	NPC312056
0.9387	High Similarity	NPC272722
0.9387	High Similarity	NPC238995
0.9353	High Similarity	NPC47883
0.9341	High Similarity	NPC174700
0.9333	High Similarity	NPC277480
0.9325	High Similarity	NPC188486
0.9286	High Similarity	NPC310794
0.9286	High Similarity	NPC473834
0.9273	High Similarity	NPC37183
0.9235	High Similarity	NPC23553
0.9235	High Similarity	NPC77179
0.9231	High Similarity	NPC227906
0.9222	High Similarity	NPC247136
0.9212	High Similarity	NPC133065
0.9202	High Similarity	NPC195832
0.9202	High Similarity	NPC196879
0.9202	High Similarity	NPC16935
0.92	High Similarity	NPC60848
0.9191	High Similarity	NPC226725
0.9186	High Similarity	NPC240508
0.9186	High Similarity	NPC228209
0.9172	High Similarity	NPC149846
0.9167	High Similarity	NPC28042
0.9167	High Similarity	NPC131866
0.9157	High Similarity	NPC39306
0.9146	High Similarity	NPC246478
0.9143	High Similarity	NPC295436
0.9138	High Similarity	NPC248315
0.9133	High Similarity	NPC154527
0.9123	High Similarity	NPC221820
0.9123	High Similarity	NPC246877
0.9118	High Similarity	NPC289244
0.9112	High Similarity	NPC28589
0.9112	High Similarity	NPC248593
0.9107	High Similarity	NPC202470
0.9096	High Similarity	NPC270837
0.908	High Similarity	NPC45131
0.908	High Similarity	NPC472461
0.9075	High Similarity	NPC246153
0.9075	High Similarity	NPC8927
0.9075	High Similarity	NPC471842
0.9064	High Similarity	NPC471841
0.9059	High Similarity	NPC261471
0.9036	High Similarity	NPC81679
0.9036	High Similarity	NPC294965
0.903	High Similarity	NPC476980
0.9029	High Similarity	NPC240808
0.9024	High Similarity	NPC36852
0.9024	High Similarity	NPC110070
0.9024	High Similarity	NPC262286
0.9024	High Similarity	NPC203891
0.9024	High Similarity	NPC78225
0.9024	High Similarity	NPC101830
0.9023	High Similarity	NPC71260
0.9018	High Similarity	NPC268008
0.9017	High Similarity	NPC475996
0.9006	High Similarity	NPC99591
0.8994	High Similarity	NPC152477
0.8982	High Similarity	NPC236132
0.8982	High Similarity	NPC470459
0.8982	High Similarity	NPC41301
0.8976	High Similarity	NPC258331
0.8976	High Similarity	NPC66288
0.8976	High Similarity	NPC311740
0.897	High Similarity	NPC176300
0.897	High Similarity	NPC300943
0.897	High Similarity	NPC261004
0.897	High Similarity	NPC193842
0.897	High Similarity	NPC18772
0.897	High Similarity	NPC105242
0.897	High Similarity	NPC115798
0.897	High Similarity	NPC152166
0.897	High Similarity	NPC143828
0.897	High Similarity	NPC130894
0.897	High Similarity	NPC204854
0.897	High Similarity	NPC191459
0.897	High Similarity	NPC253634
0.897	High Similarity	NPC7846
0.897	High Similarity	NPC19687
0.897	High Similarity	NPC288669
0.897	High Similarity	NPC4481
0.897	High Similarity	NPC25495
0.897	High Similarity	NPC9609
0.897	High Similarity	NPC22472
0.897	High Similarity	NPC18607
0.8963	High Similarity	NPC191146
0.8963	High Similarity	NPC49824
0.8963	High Similarity	NPC266960
0.8963	High Similarity	NPC138243
0.8963	High Similarity	NPC68093
0.8963	High Similarity	NPC43243
0.8963	High Similarity	NPC245546
0.8963	High Similarity	NPC265511
0.8963	High Similarity	NPC292107
0.896	High Similarity	NPC476273
0.8957	High Similarity	NPC189130
0.8947	High Similarity	NPC117450
0.8947	High Similarity	NPC233956
0.8941	High Similarity	NPC78830
0.8941	High Similarity	NPC102277
0.8941	High Similarity	NPC218533
0.8941	High Similarity	NPC279209
0.8935	High Similarity	NPC241820
0.8935	High Similarity	NPC186392
0.8929	High Similarity	NPC470457
0.8929	High Similarity	NPC326520
0.8929	High Similarity	NPC472277
0.8929	High Similarity	NPC26386
0.8929	High Similarity	NPC291110
0.8922	High Similarity	NPC472448
0.8922	High Similarity	NPC83922
0.8916	High Similarity	NPC56085
0.8916	High Similarity	NPC84571
0.8916	High Similarity	NPC14353
0.8916	High Similarity	NPC228785
0.8909	High Similarity	NPC287979
0.8909	High Similarity	NPC476981
0.8909	High Similarity	NPC75215
0.8909	High Similarity	NPC7973
0.8909	High Similarity	NPC78302
0.8909	High Similarity	NPC29841
0.8909	High Similarity	NPC246647
0.8909	High Similarity	NPC305663
0.8909	High Similarity	NPC93376
0.8909	High Similarity	NPC212967
0.8909	High Similarity	NPC224137
0.8909	High Similarity	NPC164110
0.8909	High Similarity	NPC96342
0.8909	High Similarity	NPC235215
0.8909	High Similarity	NPC163524
0.8909	High Similarity	NPC472438
0.8909	High Similarity	NPC176665
0.8909	High Similarity	NPC227192
0.8909	High Similarity	NPC189179
0.8902	High Similarity	NPC189960
0.8902	High Similarity	NPC57674
0.8902	High Similarity	NPC20830
0.8902	High Similarity	NPC230149
0.8902	High Similarity	NPC168247
0.8902	High Similarity	NPC32557
0.8902	High Similarity	NPC152951
0.8902	High Similarity	NPC256612
0.8902	High Similarity	NPC44079
0.8902	High Similarity	NPC133392
0.8902	High Similarity	NPC113906
0.8902	High Similarity	NPC201451
0.8902	High Similarity	NPC26227
0.8902	High Similarity	NPC117992
0.8896	High Similarity	NPC304954
0.8896	High Similarity	NPC125300
0.8895	High Similarity	NPC245975
0.8889	High Similarity	NPC158226
0.8889	High Similarity	NPC121333
0.8882	High Similarity	NPC163130
0.8882	High Similarity	NPC242395
0.8882	High Similarity	NPC211309
0.8882	High Similarity	NPC165979
0.8882	High Similarity	NPC280493
0.8876	High Similarity	NPC272560
0.8876	High Similarity	NPC37870
0.8876	High Similarity	NPC470462
0.8876	High Similarity	NPC170245
0.8876	High Similarity	NPC235610
0.8869	High Similarity	NPC329669
0.8869	High Similarity	NPC197168
0.8869	High Similarity	NPC472278
0.8869	High Similarity	NPC124038
0.8869	High Similarity	NPC472281
0.8869	High Similarity	NPC473313
0.8869	High Similarity	NPC220313
0.8869	High Similarity	NPC205265
0.8869	High Similarity	NPC18100
0.8869	High Similarity	NPC472582
0.8862	High Similarity	NPC278052
0.8862	High Similarity	NPC167678
0.8862	High Similarity	NPC259456
0.8862	High Similarity	NPC472275

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 NPC49667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	998
0.2-0.3	1793
0.3-0.4	2729
0.4-0.5	1767
0.5-0.6	936
0.6-0.7	332
0.7-0.8	129
0.8-0.85	22
0.85-0.9	18
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8963	High Similarity	NPD3882	Suspended
0.8841	High Similarity	NPD2801	Approved
0.8639	High Similarity	NPD1247	Approved
0.8614	High Similarity	NPD2393	Clinical (unspecified phase)
0.8596	High Similarity	NPD6168	Clinical (unspecified phase)
0.8596	High Similarity	NPD6166	Phase 2
0.8596	High Similarity	NPD6167	Clinical (unspecified phase)
0.8588	High Similarity	NPD6232	Discontinued
0.858	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD1934	Approved
0.8547	High Similarity	NPD7473	Discontinued
0.8448	Intermediate Similarity	NPD5844	Phase 1
0.843	Intermediate Similarity	NPD3926	Phase 2
0.8415	Intermediate Similarity	NPD1512	Approved
0.8391	Intermediate Similarity	NPD3818	Discontinued
0.8354	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD3817	Phase 2
0.8305	Intermediate Similarity	NPD6559	Discontinued
0.8304	Intermediate Similarity	NPD919	Approved
0.8293	Intermediate Similarity	NPD1511	Approved
0.8258	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7075	Discontinued
0.8208	Intermediate Similarity	NPD6959	Discontinued
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD3749	Approved
0.8107	Intermediate Similarity	NPD6599	Discontinued
0.8087	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD6797	Phase 2
0.8045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD7074	Phase 3
0.7964	Intermediate Similarity	NPD6799	Approved
0.7956	Intermediate Similarity	NPD7808	Phase 3
0.7933	Intermediate Similarity	NPD7054	Approved
0.7919	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5402	Approved
0.7889	Intermediate Similarity	NPD7472	Approved
0.7874	Intermediate Similarity	NPD7768	Phase 2
0.7865	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7819	Suspended
0.7861	Intermediate Similarity	NPD1465	Phase 2
0.7849	Intermediate Similarity	NPD7411	Suspended
0.7833	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2344	Approved
0.7811	Intermediate Similarity	NPD2533	Approved
0.7811	Intermediate Similarity	NPD2532	Approved
0.7811	Intermediate Similarity	NPD2534	Approved
0.7807	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1607	Approved
0.7771	Intermediate Similarity	NPD1549	Phase 2
0.773	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD2800	Approved
0.7719	Intermediate Similarity	NPD920	Approved
0.7719	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7669	Intermediate Similarity	NPD943	Approved
0.7669	Intermediate Similarity	NPD1240	Approved
0.7651	Intermediate Similarity	NPD2796	Approved
0.7651	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD7390	Discontinued
0.7633	Intermediate Similarity	NPD2309	Approved
0.763	Intermediate Similarity	NPD3226	Approved
0.7619	Intermediate Similarity	NPD1243	Approved
0.7602	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD8434	Phase 2
0.759	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6234	Discontinued
0.7582	Intermediate Similarity	NPD3751	Discontinued
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3787	Discontinued
0.7442	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6779	Approved
0.7436	Intermediate Similarity	NPD6780	Approved
0.7436	Intermediate Similarity	NPD6781	Approved
0.7436	Intermediate Similarity	NPD6777	Approved
0.7436	Intermediate Similarity	NPD6782	Approved
0.7436	Intermediate Similarity	NPD6776	Approved
0.7436	Intermediate Similarity	NPD6778	Approved
0.7433	Intermediate Similarity	NPD8313	Approved
0.7433	Intermediate Similarity	NPD8312	Approved
0.7427	Intermediate Similarity	NPD6190	Approved
0.7411	Intermediate Similarity	NPD7435	Discontinued
0.7401	Intermediate Similarity	NPD37	Approved
0.7399	Intermediate Similarity	NPD5401	Approved
0.7396	Intermediate Similarity	NPD1471	Phase 3
0.7396	Intermediate Similarity	NPD2346	Discontinued
0.7374	Intermediate Similarity	NPD4965	Approved
0.7374	Intermediate Similarity	NPD4966	Approved
0.7374	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD3750	Approved
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7353	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1551	Phase 2
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD8150	Discontinued
0.7305	Intermediate Similarity	NPD230	Phase 1
0.7305	Intermediate Similarity	NPD447	Suspended
0.7297	Intermediate Similarity	NPD7228	Approved
0.7287	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7870	Phase 2
0.7286	Intermediate Similarity	NPD7871	Phase 2
0.7282	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7268	Intermediate Similarity	NPD7229	Phase 3
0.7268	Intermediate Similarity	NPD5710	Approved
0.7268	Intermediate Similarity	NPD5711	Approved
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1613	Approved
0.724	Intermediate Similarity	NPD4287	Approved
0.7236	Intermediate Similarity	NPD7697	Approved
0.7236	Intermediate Similarity	NPD7698	Approved
0.7236	Intermediate Similarity	NPD7696	Phase 3
0.7235	Intermediate Similarity	NPD6099	Approved
0.7235	Intermediate Similarity	NPD5404	Approved
0.7235	Intermediate Similarity	NPD6100	Approved
0.7235	Intermediate Similarity	NPD5405	Approved
0.7235	Intermediate Similarity	NPD5408	Approved
0.7235	Intermediate Similarity	NPD5406	Approved
0.7228	Intermediate Similarity	NPD8151	Discontinued
0.7204	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7874	Approved
0.7192	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD2403	Approved
0.7181	Intermediate Similarity	NPD5953	Discontinued
0.7179	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD6534	Approved
0.7178	Intermediate Similarity	NPD7701	Phase 2
0.7177	Intermediate Similarity	NPD7907	Approved
0.7169	Intermediate Similarity	NPD3027	Phase 3
0.7168	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7286	Phase 2
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2296	Approved
0.7126	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2313	Discontinued
0.7112	Intermediate Similarity	NPD2163	Approved
0.7083	Intermediate Similarity	NPD6233	Phase 2
0.7081	Intermediate Similarity	NPD4665	Approved
0.7081	Intermediate Similarity	NPD4111	Phase 1
0.7079	Intermediate Similarity	NPD1653	Approved
0.7076	Intermediate Similarity	NPD3748	Approved
0.7073	Intermediate Similarity	NPD7801	Approved
0.7072	Intermediate Similarity	NPD5761	Phase 2
0.7072	Intermediate Similarity	NPD5760	Phase 2
0.7071	Intermediate Similarity	NPD7699	Phase 2
0.7071	Intermediate Similarity	NPD7700	Phase 2
0.7066	Intermediate Similarity	NPD4625	Phase 3
0.7059	Intermediate Similarity	NPD6651	Approved
0.705	Intermediate Similarity	NPD2493	Approved
0.705	Intermediate Similarity	NPD2494	Approved
0.7048	Intermediate Similarity	NPD9494	Approved
0.7039	Intermediate Similarity	NPD7458	Discontinued
0.7024	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6798	Discontinued
0.7021	Intermediate Similarity	NPD7177	Discontinued
0.7015	Intermediate Similarity	NPD6823	Phase 2
0.7012	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7005	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1933	Approved
0.6971	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7003	Approved
0.6965	Remote Similarity	NPD3450	Approved
0.6965	Remote Similarity	NPD3452	Approved
0.6963	Remote Similarity	NPD7685	Pre-registration
0.6952	Remote Similarity	NPD5242	Approved
0.6946	Remote Similarity	NPD4582	Approved
0.6946	Remote Similarity	NPD4583	Approved
0.6941	Remote Similarity	NPD4060	Phase 1
0.6934	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1470	Approved
0.6923	Remote Similarity	NPD6279	Approved
0.6923	Remote Similarity	NPD3764	Approved
0.6923	Remote Similarity	NPD6280	Approved
0.6919	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6355	Discontinued
0.6897	Remote Similarity	NPD4002	Approved
0.6897	Remote Similarity	NPD4004	Approved
0.6885	Remote Similarity	NPD8455	Phase 2
0.6884	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4361	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data