NPASS Compound

Structure

CID307518 OpenBabel06191716112D 35 38 0 0 1 0 0 0 0 0999 V2000 -8.6603 -3.0000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -4.3301 -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 2 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 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -0.8660 1.5000 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 31 1 0 0 0 0 2 32 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 24 1 0 0 0 0 8 10 2 0 0 0 0 8 33 1 0 0 0 0 9 10 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 25 1 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 13 33 1 0 0 0 0 14 22 2 0 0 0 0 14 34 1 0 0 0 0 15 7 1 1 0 0 0 15 18 1 0 0 0 0 15 35 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 26 2 0 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 23 1 0 0 0 0 21 30 1 6 0 0 0 22 32 1 0 0 0 0 23 34 1 1 0 0 0 23 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.13
Volume:	456.529
LogP:	0.445
LogD:	0.843
LogS:	-4.059
# Rotatable Bonds:	6
TPSA:	188.51
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	4.024
Fsp3:	0.348
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.271
MDCK Permeability:	1.9907620298909023e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.81
Human Intestinal Absorption (HIA):	0.505
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.688

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	81.62493133544922%
Volume Distribution (VD):	0.671
Pgp-substrate:	19.13221549987793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.743
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	4.878
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.299
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.509
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.465
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC307518

Natural Product ID:	NPC307518
*Common Name:**	Iristectorin A
IUPAC Name:	5-hydroxy-3-(3-hydroxy-4-methoxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	HFODKTZIQVSGJO-ZTATXHNCSA-N
Standard InCHI:	InChI=1S/C23H24O12/c1-31-12-4-3-9(5-11(12)25)10-8-33-13-6-14(22(32-2)19(28)16(13)17(10)26)34-23-21(30)20(29)18(27)15(7-24)35-23/h3-6,8,15,18,20-21,23-25,27-30H,7H2,1-2H3/t15-,18-,20+,21-,23-/m1/s1
SMILES:	COc1ccc(cc1O)c1coc2cc(c(c(c2c1=O)O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511453
PubChem CID:	11968629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid O-glycosides

*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
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075762]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	rhizomes	Thai	n.a.	PMID[15787436]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465599]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23189738]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24433009]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25036154]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28032759]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31246464]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917289]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8881	Centipeda minima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14417	Iris tectorum	Species	Iridaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	26.1	uM	PMID[483263]

☑ 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 NPC307518 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	440
0.1-0.2	1775
0.2-0.3	3895
0.3-0.4	9614
0.4-0.5	8769
0.5-0.6	4133
0.6-0.7	5148
0.7-0.8	5491
0.8-0.85	1687
0.85-0.9	1232
0.9-0.95	434
0.95-1	79

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC205076
1.0	High Similarity	NPC48773
0.9938	High Similarity	NPC105511
0.9938	High Similarity	NPC224462
0.9875	High Similarity	NPC201292
0.9875	High Similarity	NPC226294
0.9875	High Similarity	NPC469931
0.9875	High Similarity	NPC186807
0.9875	High Similarity	NPC58053
0.9875	High Similarity	NPC93337
0.9875	High Similarity	NPC475942
0.9875	High Similarity	NPC45638
0.9875	High Similarity	NPC105025
0.9814	High Similarity	NPC183357
0.9814	High Similarity	NPC21190
0.9814	High Similarity	NPC44558
0.9814	High Similarity	NPC474434
0.9814	High Similarity	NPC22195
0.9814	High Similarity	NPC471416
0.9814	High Similarity	NPC34287
0.9812	High Similarity	NPC229729
0.9812	High Similarity	NPC58716
0.9812	High Similarity	NPC146792
0.9812	High Similarity	NPC45618
0.9812	High Similarity	NPC135345
0.9753	High Similarity	NPC254540
0.9753	High Similarity	NPC211594
0.9753	High Similarity	NPC476405
0.9753	High Similarity	NPC117260
0.9753	High Similarity	NPC172807
0.9752	High Similarity	NPC95855
0.9752	High Similarity	NPC170675
0.9752	High Similarity	NPC472383
0.9752	High Similarity	NPC471457
0.9752	High Similarity	NPC472381
0.9752	High Similarity	NPC112755
0.9752	High Similarity	NPC210042
0.9752	High Similarity	NPC183036
0.9752	High Similarity	NPC229687
0.9693	High Similarity	NPC239549
0.9693	High Similarity	NPC21666
0.9693	High Similarity	NPC236191
0.9693	High Similarity	NPC169977
0.9693	High Similarity	NPC204693
0.9693	High Similarity	NPC101026
0.9693	High Similarity	NPC24043
0.9693	High Similarity	NPC45522
0.9693	High Similarity	NPC42773
0.9693	High Similarity	NPC51774
0.9691	High Similarity	NPC245014
0.9691	High Similarity	NPC282987
0.9691	High Similarity	NPC84265
0.9691	High Similarity	NPC231194
0.9691	High Similarity	NPC51326
0.9689	High Similarity	NPC93099
0.9689	High Similarity	NPC45400
0.9688	High Similarity	NPC165720
0.9688	High Similarity	NPC311830
0.9688	High Similarity	NPC22832
0.9636	High Similarity	NPC168584
0.9634	High Similarity	NPC477848
0.9634	High Similarity	NPC472607
0.9632	High Similarity	NPC3583
0.9632	High Similarity	NPC267254
0.9632	High Similarity	NPC301683
0.9632	High Similarity	NPC472386
0.9632	High Similarity	NPC235575
0.9632	High Similarity	NPC259152
0.9632	High Similarity	NPC475155
0.9627	High Similarity	NPC236934
0.9627	High Similarity	NPC5778
0.9627	High Similarity	NPC99957
0.9627	High Similarity	NPC181616
0.9625	High Similarity	NPC284960
0.9625	High Similarity	NPC88023
0.9625	High Similarity	NPC191306
0.9625	High Similarity	NPC19709
0.9625	High Similarity	NPC270335
0.9625	High Similarity	NPC309025
0.9625	High Similarity	NPC94777
0.9625	High Similarity	NPC168822
0.9625	High Similarity	NPC222936
0.9625	High Similarity	NPC243930
0.9625	High Similarity	NPC88043
0.9576	High Similarity	NPC169733
0.9576	High Similarity	NPC198324
0.9576	High Similarity	NPC472991
0.9576	High Similarity	NPC472992
0.9576	High Similarity	NPC257714
0.9576	High Similarity	NPC233994
0.9576	High Similarity	NPC211532
0.9576	High Similarity	NPC472385
0.9571	High Similarity	NPC212748
0.9571	High Similarity	NPC206123
0.9568	High Similarity	NPC116745
0.9563	High Similarity	NPC127782
0.9563	High Similarity	NPC473043
0.9563	High Similarity	NPC189142
0.9563	High Similarity	NPC300537
0.9563	High Similarity	NPC77660
0.9518	High Similarity	NPC476621
0.9518	High Similarity	NPC476623
0.9518	High Similarity	NPC476620
0.9518	High Similarity	NPC472387
0.9518	High Similarity	NPC476618
0.9518	High Similarity	NPC476619
0.9518	High Similarity	NPC476622
0.9515	High Similarity	NPC264735
0.9515	High Similarity	NPC115760
0.9515	High Similarity	NPC102028
0.9515	High Similarity	NPC142996
0.9515	High Similarity	NPC43211
0.9515	High Similarity	NPC49344
0.9515	High Similarity	NPC237435
0.9515	High Similarity	NPC210094
0.9515	High Similarity	NPC135277
0.9515	High Similarity	NPC101191
0.9512	High Similarity	NPC156977
0.9512	High Similarity	NPC256760
0.9509	High Similarity	NPC471287
0.9509	High Similarity	NPC195257
0.9509	High Similarity	NPC225434
0.9509	High Similarity	NPC209296
0.9509	High Similarity	NPC203050
0.9509	High Similarity	NPC223747
0.9509	High Similarity	NPC120099
0.9509	High Similarity	NPC219904
0.9506	High Similarity	NPC115674
0.9506	High Similarity	NPC21100
0.9506	High Similarity	NPC197285
0.9506	High Similarity	NPC210073
0.9503	High Similarity	NPC29830
0.9503	High Similarity	NPC127415
0.95	High Similarity	NPC182045
0.9464	High Similarity	NPC36138
0.9461	High Similarity	NPC473682
0.9461	High Similarity	NPC126784
0.9461	High Similarity	NPC470443
0.9461	High Similarity	NPC470444
0.9461	High Similarity	NPC110941
0.9461	High Similarity	NPC241423
0.9461	High Similarity	NPC473571
0.9458	High Similarity	NPC472380
0.9458	High Similarity	NPC65563
0.9458	High Similarity	NPC472384
0.9458	High Similarity	NPC268533
0.9458	High Similarity	NPC8573
0.9458	High Similarity	NPC470949
0.9458	High Similarity	NPC472382
0.9455	High Similarity	NPC172033
0.9455	High Similarity	NPC4390
0.9455	High Similarity	NPC472993
0.9455	High Similarity	NPC175230
0.9455	High Similarity	NPC88560
0.9455	High Similarity	NPC208668
0.9451	High Similarity	NPC105095
0.9451	High Similarity	NPC204937
0.9451	High Similarity	NPC177731
0.9451	High Similarity	NPC79056
0.9451	High Similarity	NPC78734
0.9451	High Similarity	NPC149011
0.9451	High Similarity	NPC44328
0.9451	High Similarity	NPC293004
0.9451	High Similarity	NPC150767
0.9448	High Similarity	NPC243877
0.9448	High Similarity	NPC84362
0.9448	High Similarity	NPC317489
0.9448	High Similarity	NPC471288
0.9448	High Similarity	NPC325555
0.9448	High Similarity	NPC52550
0.9448	High Similarity	NPC223424
0.9448	High Similarity	NPC265530
0.9448	High Similarity	NPC226304
0.9448	High Similarity	NPC477502
0.9448	High Similarity	NPC127546
0.9448	High Similarity	NPC173637
0.9444	High Similarity	NPC277205
0.9437	High Similarity	NPC110349
0.9408	High Similarity	NPC470416
0.9408	High Similarity	NPC148710
0.9405	High Similarity	NPC473071
0.9405	High Similarity	NPC473073
0.9401	High Similarity	NPC475261
0.9394	High Similarity	NPC261254
0.9394	High Similarity	NPC175107
0.9394	High Similarity	NPC153755
0.9394	High Similarity	NPC190003
0.939	High Similarity	NPC293629
0.939	High Similarity	NPC86008
0.939	High Similarity	NPC270578
0.939	High Similarity	NPC61791
0.939	High Similarity	NPC52382
0.939	High Similarity	NPC43587
0.9387	High Similarity	NPC274618
0.9387	High Similarity	NPC135599
0.9387	High Similarity	NPC56077
0.9387	High Similarity	NPC118284
0.9387	High Similarity	NPC277174
0.9387	High Similarity	NPC73855
0.9387	High Similarity	NPC145038

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 NPC307518 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	944
0.2-0.3	1905
0.3-0.4	2729
0.4-0.5	1817
0.5-0.6	880
0.6-0.7	306
0.7-0.8	133
0.8-0.85	21
0.85-0.9	8
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD3818	Discontinued
0.9515	High Similarity	NPD4338	Clinical (unspecified phase)
0.9509	High Similarity	NPD7054	Approved
0.9451	High Similarity	NPD7074	Phase 3
0.9451	High Similarity	NPD7472	Approved
0.9313	High Similarity	NPD4381	Clinical (unspecified phase)
0.9277	High Similarity	NPD6797	Phase 2
0.9222	High Similarity	NPD7251	Discontinued
0.9167	High Similarity	NPD7808	Phase 3
0.9125	High Similarity	NPD2801	Approved
0.9062	High Similarity	NPD1934	Approved
0.8976	High Similarity	NPD6166	Phase 2
0.8976	High Similarity	NPD6167	Clinical (unspecified phase)
0.8976	High Similarity	NPD6168	Clinical (unspecified phase)
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8817	High Similarity	NPD7804	Clinical (unspecified phase)
0.878	High Similarity	NPD4868	Clinical (unspecified phase)
0.8704	High Similarity	NPD4380	Phase 2
0.8667	High Similarity	NPD3882	Suspended
0.8623	High Similarity	NPD5494	Approved
0.8606	High Similarity	NPD3817	Phase 2
0.8562	High Similarity	NPD1511	Approved
0.8555	High Similarity	NPD6559	Discontinued
0.8494	Intermediate Similarity	NPD5402	Approved
0.8466	Intermediate Similarity	NPD1653	Approved
0.8457	Intermediate Similarity	NPD1512	Approved
0.8393	Intermediate Similarity	NPD7075	Discontinued
0.8391	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD5844	Phase 1
0.8263	Intermediate Similarity	NPD6801	Discontinued
0.825	Intermediate Similarity	NPD1549	Phase 2
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1465	Phase 2
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD7685	Pre-registration
0.8125	Intermediate Similarity	NPD2796	Approved
0.8122	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD7411	Suspended
0.8092	Intermediate Similarity	NPD6232	Discontinued
0.8072	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5403	Approved
0.8063	Intermediate Similarity	NPD1510	Phase 2
0.8061	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7473	Discontinued
0.8011	Intermediate Similarity	NPD3751	Discontinued
0.8011	Intermediate Similarity	NPD7228	Approved
0.8	Intermediate Similarity	NPD6799	Approved
0.7956	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5401	Approved
0.7944	Intermediate Similarity	NPD8313	Approved
0.7944	Intermediate Similarity	NPD8312	Approved
0.7931	Intermediate Similarity	NPD7199	Phase 2
0.7931	Intermediate Similarity	NPD1247	Approved
0.7931	Intermediate Similarity	NPD6959	Discontinued
0.7926	Intermediate Similarity	NPD6782	Approved
0.7926	Intermediate Similarity	NPD6776	Approved
0.7926	Intermediate Similarity	NPD6780	Approved
0.7926	Intermediate Similarity	NPD6781	Approved
0.7926	Intermediate Similarity	NPD6777	Approved
0.7926	Intermediate Similarity	NPD6778	Approved
0.7926	Intermediate Similarity	NPD6779	Approved
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.7886	Intermediate Similarity	NPD3787	Discontinued
0.7836	Intermediate Similarity	NPD37	Approved
0.7824	Intermediate Similarity	NPD6599	Discontinued
0.7818	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD943	Approved
0.7812	Intermediate Similarity	NPD1613	Approved
0.7812	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1240	Approved
0.7803	Intermediate Similarity	NPD4965	Approved
0.7803	Intermediate Similarity	NPD4967	Phase 2
0.7803	Intermediate Similarity	NPD4966	Approved
0.7801	Intermediate Similarity	NPD7435	Discontinued
0.7797	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7584	Approved
0.7744	Intermediate Similarity	NPD7266	Discontinued
0.774	Intermediate Similarity	NPD3926	Phase 2
0.774	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1607	Approved
0.7714	Intermediate Similarity	NPD919	Approved
0.7711	Intermediate Similarity	NPD3750	Approved
0.7708	Intermediate Similarity	NPD7697	Approved
0.7708	Intermediate Similarity	NPD7696	Phase 3
0.7708	Intermediate Similarity	NPD7698	Approved
0.7692	Intermediate Similarity	NPD8151	Discontinued
0.7683	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7870	Phase 2
0.7668	Intermediate Similarity	NPD7871	Phase 2
0.7665	Intermediate Similarity	NPD6190	Approved
0.766	Intermediate Similarity	NPD6534	Approved
0.766	Intermediate Similarity	NPD6535	Approved
0.7657	Intermediate Similarity	NPD3749	Approved
0.7656	Intermediate Similarity	NPD6823	Phase 2
0.7654	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD1933	Approved
0.7641	Intermediate Similarity	NPD7701	Phase 2
0.7625	Intermediate Similarity	NPD3027	Phase 3
0.7614	Intermediate Similarity	NPD7783	Phase 2
0.7614	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD7768	Phase 2
0.759	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7874	Approved
0.7562	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD447	Suspended
0.7541	Intermediate Similarity	NPD7240	Approved
0.7539	Intermediate Similarity	NPD7700	Phase 2
0.7539	Intermediate Similarity	NPD7699	Phase 2
0.7525	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8455	Phase 2
0.747	Intermediate Similarity	NPD1551	Phase 2
0.7461	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD920	Approved
0.744	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6844	Discontinued
0.7427	Intermediate Similarity	NPD2532	Approved
0.7427	Intermediate Similarity	NPD2534	Approved
0.7427	Intermediate Similarity	NPD2533	Approved
0.7421	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6212	Phase 3
0.7421	Intermediate Similarity	NPD6213	Phase 3
0.741	Intermediate Similarity	NPD3748	Approved
0.7396	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7374	Intermediate Similarity	NPD7585	Approved
0.7362	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3226	Approved
0.734	Intermediate Similarity	NPD8150	Discontinued
0.734	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD2800	Approved
0.7326	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7583	Approved
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD9494	Approved
0.7283	Intermediate Similarity	NPD7286	Phase 2
0.7257	Intermediate Similarity	NPD7458	Discontinued
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7235	Intermediate Similarity	NPD1243	Approved
0.7235	Intermediate Similarity	NPD6674	Discontinued
0.7231	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2798	Approved
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7219	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2346	Discontinued
0.7219	Intermediate Similarity	NPD2344	Approved
0.7209	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD4363	Phase 3
0.7202	Intermediate Similarity	NPD4360	Phase 2
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.7198	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7680	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD6099	Approved
0.7158	Intermediate Similarity	NPD5242	Approved
0.7151	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7128	Intermediate Similarity	NPD7549	Discontinued
0.7125	Intermediate Similarity	NPD1091	Approved
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6651	Approved
0.7069	Intermediate Similarity	NPD7390	Discontinued
0.7062	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1203	Approved
0.7052	Intermediate Similarity	NPD2309	Approved
0.7049	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5005	Approved
0.7035	Intermediate Similarity	NPD1652	Phase 2
0.7035	Intermediate Similarity	NPD5006	Approved
0.7031	Intermediate Similarity	NPD6841	Approved
0.7031	Intermediate Similarity	NPD6842	Approved
0.7031	Intermediate Similarity	NPD6843	Phase 3
0.7029	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8059	Phase 3
0.7027	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5124	Phase 1
0.7024	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5710	Approved
0.7011	Intermediate Similarity	NPD5711	Approved
0.7006	Intermediate Similarity	NPD6233	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