NPASS Compound

Structure

NPC469794 OpenBabel07101718202D 29 33 0 0 1 0 0 0 0 0999 V2000 -4.0519 0.1910 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 2.5827 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9285 2.1303 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 -5.5921 0.5477 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 -5.1854 1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7946 1.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7081 2.0371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6036 1.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5867 0.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 15 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 29 1 0 0 0 0 13 21 1 0 0 0 0 13 24 2 0 0 0 0 14 15 1 0 0 0 0 15 20 1 1 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 21 1 1 0 0 0 18 20 1 1 0 0 0 18 25 1 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 20 23 1 1 0 0 0 21 22 1 1 0 0 0 22 27 1 1 0 0 0 23 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.22
Volume:	408.414
LogP:	1.386
LogD:	1.156
LogS:	-3.671
# Rotatable Bonds:	2
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	5.199
Fsp3:	0.783
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.907
MDCK Permeability:	1.0351770470151678e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.256
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.807
Plasma Protein Binding (PPB):	66.2468490600586%
Volume Distribution (VD):	0.93
Pgp-substrate:	23.637712478637695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.23
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	8.533
Half-life (T1/2):	0.206

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.59
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.804
Carcinogencity:	0.873
Eye Corrosion:	0.006
Eye Irritation:	0.018
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC469794

Natural Product ID:	NPC469794
*Common Name:**	Antiarigenin
IUPAC Name:	(5R,8R,9S,10S,12R,13S,14S,17R)-5,12,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:	Antiarigenin
Standard InCHIKey:	MCVOHUJEDFIRQZ-OMCNTIPVSA-N
Standard InCHI:	InChI=1S/C23H32O6/c1-20-15(14-10-19(26)29-12-14)5-9-23(20,28)16-4-8-22(27)7-3-2-6-21(22,13-24)17(16)11-18(20)25/h10,13,15-18,25,27-28H,2-9,11-12H2,1H3/t15-,16-,17+,18-,20+,21+,22-,23+/m1/s1
SMILES:	CC12C(CCC1(C3CCC4(CCCCC4(C3CC2O)C=O)O)O)C5=CC(=O)OC5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172849
PubChem CID:	49799517
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives

*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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	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
ED50	10
Others	3

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.41	ug ml-1	PMID[567120]
NPT308	Cell Line	CAKI-1	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[567120]
NPT309	Cell Line	1A9	Homo sapiens	ED50	=	0.12	ug ml-1	PMID[567120]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[567120]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[567120]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.59	ug ml-1	PMID[567120]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	5.3	ug ml-1	PMID[567120]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.05	uM	PMID[567119]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	121.0	%	PMID[567119]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	20.0	n.a.	PMID[567119]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.5	ug ml-1	PMID[567120]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.6	ug ml-1	PMID[567120]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.1	ug ml-1	PMID[567120]

☑ 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 NPC469794 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	234
0.1-0.2	1405
0.2-0.3	4405
0.3-0.4	7915
0.4-0.5	12954
0.5-0.6	6139
0.6-0.7	6505
0.7-0.8	2801
0.8-0.85	260
0.85-0.9	70
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC72772
0.9273	High Similarity	NPC196931
0.9043	High Similarity	NPC55602
0.8983	High Similarity	NPC469751
0.8983	High Similarity	NPC471361
0.8983	High Similarity	NPC180079
0.8983	High Similarity	NPC284406
0.8983	High Similarity	NPC10823
0.8983	High Similarity	NPC471360
0.8983	High Similarity	NPC86159
0.8983	High Similarity	NPC471359
0.8983	High Similarity	NPC70542
0.8983	High Similarity	NPC469753
0.8983	High Similarity	NPC89514
0.8983	High Similarity	NPC469754
0.8983	High Similarity	NPC9499
0.8983	High Similarity	NPC469752
0.8983	High Similarity	NPC251866
0.8983	High Similarity	NPC469755
0.8983	High Similarity	NPC6108
0.8983	High Similarity	NPC17896
0.8983	High Similarity	NPC219085
0.8983	High Similarity	NPC197707
0.8983	High Similarity	NPC471358
0.8983	High Similarity	NPC471352
0.8962	High Similarity	NPC97487
0.8962	High Similarity	NPC10232
0.8962	High Similarity	NPC196471
0.8962	High Similarity	NPC187302
0.8962	High Similarity	NPC189588
0.8947	High Similarity	NPC184555
0.8818	High Similarity	NPC179642
0.8814	High Similarity	NPC179412
0.8814	High Similarity	NPC469757
0.8814	High Similarity	NPC146456
0.8814	High Similarity	NPC471356
0.8814	High Similarity	NPC117702
0.8814	High Similarity	NPC471357
0.8785	High Similarity	NPC112009
0.8774	High Similarity	NPC25177
0.8774	High Similarity	NPC222875
0.8774	High Similarity	NPC295110
0.8774	High Similarity	NPC247701
0.8774	High Similarity	NPC268829
0.876	High Similarity	NPC116075
0.876	High Similarity	NPC247190
0.876	High Similarity	NPC146857
0.876	High Similarity	NPC469749
0.876	High Similarity	NPC32793
0.8729	High Similarity	NPC250556
0.8729	High Similarity	NPC469750
0.8727	High Similarity	NPC257082
0.8727	High Similarity	NPC285298
0.8716	High Similarity	NPC263729
0.8689	High Similarity	NPC329636
0.8667	High Similarity	NPC231529
0.8624	High Similarity	NPC119855
0.8624	High Similarity	NPC220217
0.8621	High Similarity	NPC472004
0.8618	High Similarity	NPC194716
0.8611	High Similarity	NPC120321
0.8611	High Similarity	NPC180204
0.8611	High Similarity	NPC160583
0.8607	High Similarity	NPC88668
0.8598	High Similarity	NPC471412
0.8559	High Similarity	NPC475030
0.8559	High Similarity	NPC27363
0.8548	High Similarity	NPC329675
0.8548	High Similarity	NPC59288
0.8525	High Similarity	NPC93416
0.8519	High Similarity	NPC193934
0.8519	High Similarity	NPC271980
0.8512	High Similarity	NPC276838
0.8512	High Similarity	NPC125077
0.8512	High Similarity	NPC329986
0.8512	High Similarity	NPC232785
0.8512	High Similarity	NPC140092
0.8512	High Similarity	NPC188234
0.8505	High Similarity	NPC117685
0.8505	High Similarity	NPC471413
0.8505	High Similarity	NPC201406
0.8505	High Similarity	NPC251680
0.8496	Intermediate Similarity	NPC470063
0.8487	Intermediate Similarity	NPC233041
0.8468	Intermediate Similarity	NPC163216
0.8455	Intermediate Similarity	NPC186668
0.8455	Intermediate Similarity	NPC295366
0.8443	Intermediate Similarity	NPC16569
0.8443	Intermediate Similarity	NPC159338
0.8443	Intermediate Similarity	NPC253456
0.844	Intermediate Similarity	NPC312900
0.844	Intermediate Similarity	NPC472821
0.843	Intermediate Similarity	NPC311534
0.8426	Intermediate Similarity	NPC475099
0.8421	Intermediate Similarity	NPC52634
0.8421	Intermediate Similarity	NPC73050
0.8411	Intermediate Similarity	NPC119036
0.8403	Intermediate Similarity	NPC473979
0.8387	Intermediate Similarity	NPC248703
0.8378	Intermediate Similarity	NPC179380
0.8376	Intermediate Similarity	NPC230513
0.8374	Intermediate Similarity	NPC19124
0.8374	Intermediate Similarity	NPC42670
0.8364	Intermediate Similarity	NPC201763
0.8362	Intermediate Similarity	NPC239273
0.8361	Intermediate Similarity	NPC91
0.8349	Intermediate Similarity	NPC22388
0.8349	Intermediate Similarity	NPC476081
0.8349	Intermediate Similarity	NPC162973
0.8349	Intermediate Similarity	NPC170615
0.8348	Intermediate Similarity	NPC470953
0.8348	Intermediate Similarity	NPC178289
0.8348	Intermediate Similarity	NPC238667
0.8347	Intermediate Similarity	NPC240070
0.8347	Intermediate Similarity	NPC287423
0.8347	Intermediate Similarity	NPC329784
0.8333	Intermediate Similarity	NPC108371
0.8333	Intermediate Similarity	NPC90952
0.8333	Intermediate Similarity	NPC277769
0.8333	Intermediate Similarity	NPC476163
0.8333	Intermediate Similarity	NPC4573
0.8319	Intermediate Similarity	NPC269642
0.8306	Intermediate Similarity	NPC104585
0.8306	Intermediate Similarity	NPC476221
0.8306	Intermediate Similarity	NPC298783
0.8306	Intermediate Similarity	NPC157817
0.8306	Intermediate Similarity	NPC477709
0.8306	Intermediate Similarity	NPC225385
0.8305	Intermediate Similarity	NPC476962
0.8305	Intermediate Similarity	NPC145074
0.8305	Intermediate Similarity	NPC114939
0.8305	Intermediate Similarity	NPC41123
0.8304	Intermediate Similarity	NPC177064
0.8304	Intermediate Similarity	NPC306265
0.8291	Intermediate Similarity	NPC113448
0.8276	Intermediate Similarity	NPC266728
0.8276	Intermediate Similarity	NPC298278
0.8276	Intermediate Similarity	NPC106228
0.8276	Intermediate Similarity	NPC49492
0.8276	Intermediate Similarity	NPC138372
0.8273	Intermediate Similarity	NPC36688
0.8273	Intermediate Similarity	NPC222153
0.8261	Intermediate Similarity	NPC9848
0.8261	Intermediate Similarity	NPC962
0.8261	Intermediate Similarity	NPC312017
0.8254	Intermediate Similarity	NPC62172
0.8254	Intermediate Similarity	NPC289700
0.825	Intermediate Similarity	NPC11895
0.825	Intermediate Similarity	NPC472768
0.825	Intermediate Similarity	NPC204812
0.8235	Intermediate Similarity	NPC46570
0.823	Intermediate Similarity	NPC475941
0.823	Intermediate Similarity	NPC476759
0.823	Intermediate Similarity	NPC474243
0.823	Intermediate Similarity	NPC474901
0.8224	Intermediate Similarity	NPC29952
0.822	Intermediate Similarity	NPC42673
0.822	Intermediate Similarity	NPC476960
0.822	Intermediate Similarity	NPC475041
0.822	Intermediate Similarity	NPC312536
0.8214	Intermediate Similarity	NPC220974
0.8214	Intermediate Similarity	NPC302788
0.8211	Intermediate Similarity	NPC221414
0.8205	Intermediate Similarity	NPC55296
0.8205	Intermediate Similarity	NPC476959
0.8205	Intermediate Similarity	NPC474518
0.8182	Intermediate Similarity	NPC286519
0.8182	Intermediate Similarity	NPC124544
0.8182	Intermediate Similarity	NPC241456
0.8182	Intermediate Similarity	NPC172154
0.8182	Intermediate Similarity	NPC76866
0.8182	Intermediate Similarity	NPC214946
0.8182	Intermediate Similarity	NPC81736
0.8182	Intermediate Similarity	NPC304832
0.8182	Intermediate Similarity	NPC32868
0.8182	Intermediate Similarity	NPC88203
0.8182	Intermediate Similarity	NPC8369
0.8182	Intermediate Similarity	NPC148628
0.8182	Intermediate Similarity	NPC469790
0.8182	Intermediate Similarity	NPC246736
0.8182	Intermediate Similarity	NPC476769
0.8175	Intermediate Similarity	NPC171619
0.8174	Intermediate Similarity	NPC285956
0.8174	Intermediate Similarity	NPC69291
0.8167	Intermediate Similarity	NPC222688
0.8167	Intermediate Similarity	NPC107493
0.8167	Intermediate Similarity	NPC170538
0.8165	Intermediate Similarity	NPC37047
0.8165	Intermediate Similarity	NPC41971
0.8165	Intermediate Similarity	NPC476767
0.8165	Intermediate Similarity	NPC180733
0.8165	Intermediate Similarity	NPC94906
0.8165	Intermediate Similarity	NPC471041
0.816	Intermediate Similarity	NPC142756
0.8158	Intermediate Similarity	NPC472666
0.8158	Intermediate Similarity	NPC470496
0.8151	Intermediate Similarity	NPC154491
0.8151	Intermediate Similarity	NPC268530
0.8151	Intermediate Similarity	NPC476961
0.8151	Intermediate Similarity	NPC251226

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 NPC469794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1613
0.2-0.3	3857
0.3-0.4	2275
0.4-0.5	695
0.5-0.6	213
0.6-0.7	166
0.7-0.8	123
0.8-0.85	4
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8983	High Similarity	NPD7319	Approved
0.8729	High Similarity	NPD7507	Approved
0.8585	High Similarity	NPD7638	Approved
0.8505	High Similarity	NPD7640	Approved
0.8505	High Similarity	NPD7639	Approved
0.8142	Intermediate Similarity	NPD7320	Approved
0.8125	Intermediate Similarity	NPD5739	Approved
0.8125	Intermediate Similarity	NPD6675	Approved
0.8125	Intermediate Similarity	NPD7128	Approved
0.8125	Intermediate Similarity	NPD6402	Approved
0.7983	Intermediate Similarity	NPD7327	Approved
0.7983	Intermediate Similarity	NPD7328	Approved
0.7982	Intermediate Similarity	NPD6881	Approved
0.7982	Intermediate Similarity	NPD6899	Approved
0.7917	Intermediate Similarity	NPD7516	Approved
0.7913	Intermediate Similarity	NPD6373	Approved
0.7913	Intermediate Similarity	NPD6372	Approved
0.7895	Intermediate Similarity	NPD5697	Approved
0.7895	Intermediate Similarity	NPD5701	Approved
0.7886	Intermediate Similarity	NPD7492	Approved
0.7863	Intermediate Similarity	NPD6053	Discontinued
0.7857	Intermediate Similarity	NPD7632	Discontinued
0.7851	Intermediate Similarity	NPD6059	Approved
0.7851	Intermediate Similarity	NPD6319	Approved
0.7851	Intermediate Similarity	NPD6054	Approved
0.7845	Intermediate Similarity	NPD7290	Approved
0.7845	Intermediate Similarity	NPD7102	Approved
0.7845	Intermediate Similarity	NPD6883	Approved
0.784	Intermediate Similarity	NPD7736	Approved
0.7823	Intermediate Similarity	NPD6616	Approved
0.7807	Intermediate Similarity	NPD6008	Approved
0.7787	Intermediate Similarity	NPD8380	Approved
0.7787	Intermediate Similarity	NPD8296	Approved
0.7787	Intermediate Similarity	NPD8379	Approved
0.7787	Intermediate Similarity	NPD8335	Approved
0.7787	Intermediate Similarity	NPD8378	Approved
0.7778	Intermediate Similarity	NPD6650	Approved
0.7778	Intermediate Similarity	NPD8130	Phase 1
0.7778	Intermediate Similarity	NPD6869	Approved
0.7778	Intermediate Similarity	NPD6617	Approved
0.7778	Intermediate Similarity	NPD6847	Approved
0.7778	Intermediate Similarity	NPD6649	Approved
0.776	Intermediate Similarity	NPD7078	Approved
0.776	Intermediate Similarity	NPD8293	Discontinued
0.7759	Intermediate Similarity	NPD6014	Approved
0.7759	Intermediate Similarity	NPD6012	Approved
0.7759	Intermediate Similarity	NPD6013	Approved
0.775	Intermediate Similarity	NPD7115	Discovery
0.7724	Intermediate Similarity	NPD6370	Approved
0.7712	Intermediate Similarity	NPD6882	Approved
0.7712	Intermediate Similarity	NPD8297	Approved
0.7705	Intermediate Similarity	NPD8294	Approved
0.7705	Intermediate Similarity	NPD8377	Approved
0.7672	Intermediate Similarity	NPD6011	Approved
0.7658	Intermediate Similarity	NPD4755	Approved
0.7658	Intermediate Similarity	NPD6083	Phase 2
0.7658	Intermediate Similarity	NPD6084	Phase 2
0.7647	Intermediate Similarity	NPD4632	Approved
0.7642	Intermediate Similarity	NPD8033	Approved
0.7642	Intermediate Similarity	NPD6015	Approved
0.7642	Intermediate Similarity	NPD6016	Approved
0.7627	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5988	Approved
0.7544	Intermediate Similarity	NPD5211	Phase 2
0.7542	Intermediate Similarity	NPD4634	Approved
0.7522	Intermediate Similarity	NPD4696	Approved
0.7522	Intermediate Similarity	NPD5286	Approved
0.7522	Intermediate Similarity	NPD4700	Approved
0.7522	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7459	Intermediate Similarity	NPD6009	Approved
0.7414	Intermediate Similarity	NPD5141	Approved
0.7411	Intermediate Similarity	NPD4697	Phase 3
0.7395	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4633	Approved
0.7391	Intermediate Similarity	NPD5224	Approved
0.7391	Intermediate Similarity	NPD5226	Approved
0.7391	Intermediate Similarity	NPD5225	Approved
0.7381	Intermediate Similarity	NPD7604	Phase 2
0.7377	Intermediate Similarity	NPD6274	Approved
0.7373	Intermediate Similarity	NPD6686	Approved
0.7373	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6079	Approved
0.736	Intermediate Similarity	NPD5983	Phase 2
0.7339	Intermediate Similarity	NPD7100	Approved
0.7339	Intermediate Similarity	NPD7101	Approved
0.7328	Intermediate Similarity	NPD5175	Approved
0.7328	Intermediate Similarity	NPD5174	Approved
0.7321	Intermediate Similarity	NPD5695	Phase 3
0.7321	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5223	Approved
0.7297	Intermediate Similarity	NPD4202	Approved
0.7287	Intermediate Similarity	NPD6033	Approved
0.7281	Intermediate Similarity	NPD4225	Approved
0.7281	Intermediate Similarity	NPD5696	Approved
0.7266	Intermediate Similarity	NPD6336	Discontinued
0.7258	Intermediate Similarity	NPD6335	Approved
0.7248	Intermediate Similarity	NPD6903	Approved
0.7248	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7748	Approved
0.7222	Intermediate Similarity	NPD6909	Approved
0.7222	Intermediate Similarity	NPD5330	Approved
0.7222	Intermediate Similarity	NPD6684	Approved
0.7222	Intermediate Similarity	NPD6908	Approved
0.7222	Intermediate Similarity	NPD7334	Approved
0.7222	Intermediate Similarity	NPD7521	Approved
0.7222	Intermediate Similarity	NPD7146	Approved
0.7222	Intermediate Similarity	NPD6409	Approved
0.7207	Intermediate Similarity	NPD5693	Phase 1
0.7207	Intermediate Similarity	NPD7515	Phase 2
0.7207	Intermediate Similarity	NPD7637	Suspended
0.7203	Intermediate Similarity	NPD4768	Approved
0.7203	Intermediate Similarity	NPD4767	Approved
0.7182	Intermediate Similarity	NPD4753	Phase 2
0.7179	Intermediate Similarity	NPD4754	Approved
0.7177	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.713	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6313	Approved
0.712	Intermediate Similarity	NPD6314	Approved
0.7105	Intermediate Similarity	NPD5221	Approved
0.7105	Intermediate Similarity	NPD5222	Approved
0.7105	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7503	Approved
0.7087	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5128	Approved
0.7083	Intermediate Similarity	NPD4730	Approved
0.7083	Intermediate Similarity	NPD4729	Approved
0.7073	Intermediate Similarity	NPD8133	Approved
0.7064	Intermediate Similarity	NPD3618	Phase 1
0.7054	Intermediate Similarity	NPD8035	Phase 2
0.7054	Intermediate Similarity	NPD8034	Phase 2
0.7043	Intermediate Similarity	NPD5173	Approved
0.7043	Intermediate Similarity	NPD7902	Approved
0.7037	Intermediate Similarity	NPD3666	Approved
0.7037	Intermediate Similarity	NPD3133	Approved
0.7037	Intermediate Similarity	NPD3665	Phase 1
0.7027	Intermediate Similarity	NPD6673	Approved
0.7027	Intermediate Similarity	NPD6080	Approved
0.7027	Intermediate Similarity	NPD6904	Approved
0.7027	Intermediate Similarity	NPD6051	Approved
0.7009	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5779	Approved
0.6991	Remote Similarity	NPD5778	Approved
0.6977	Remote Similarity	NPD8328	Phase 3
0.6967	Remote Similarity	NPD5247	Approved
0.6967	Remote Similarity	NPD5248	Approved
0.6967	Remote Similarity	NPD6371	Approved
0.6967	Remote Similarity	NPD5250	Approved
0.6967	Remote Similarity	NPD5249	Phase 3
0.6967	Remote Similarity	NPD5251	Approved
0.6964	Remote Similarity	NPD5785	Approved
0.696	Remote Similarity	NPD6868	Approved
0.6937	Remote Similarity	NPD6672	Approved
0.6937	Remote Similarity	NPD5737	Approved
0.6934	Remote Similarity	NPD6334	Approved
0.6934	Remote Similarity	NPD6333	Approved
0.693	Remote Similarity	NPD6001	Approved
0.6911	Remote Similarity	NPD5215	Approved
0.6911	Remote Similarity	NPD5216	Approved
0.6911	Remote Similarity	NPD5217	Approved
0.6909	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6411	Approved
0.6881	Remote Similarity	NPD4786	Approved
0.687	Remote Similarity	NPD5210	Approved
0.687	Remote Similarity	NPD4629	Approved
0.686	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4223	Phase 3
0.6852	Remote Similarity	NPD4221	Approved
0.6829	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5169	Approved
0.6829	Remote Similarity	NPD5135	Approved
0.6822	Remote Similarity	NPD7525	Registered
0.6818	Remote Similarity	NPD5329	Approved
0.6792	Remote Similarity	NPD6114	Approved
0.6792	Remote Similarity	NPD6115	Approved
0.6792	Remote Similarity	NPD6118	Approved
0.6792	Remote Similarity	NPD6697	Approved
0.6789	Remote Similarity	NPD4788	Approved
0.6786	Remote Similarity	NPD5208	Approved
0.6783	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7900	Approved
0.6774	Remote Similarity	NPD5127	Approved
0.6757	Remote Similarity	NPD6098	Approved
0.6754	Remote Similarity	NPD5281	Approved
0.6754	Remote Similarity	NPD5284	Approved
0.6754	Remote Similarity	NPD6050	Approved
0.6727	Remote Similarity	NPD4197	Approved
0.6726	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6101	Approved
0.6724	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6067	Discontinued
0.6697	Remote Similarity	NPD3667	Approved
0.6696	Remote Similarity	NPD3573	Approved
0.6692	Remote Similarity	NPD6921	Approved
0.6689	Remote Similarity	NPD5761	Phase 2
0.6689	Remote Similarity	NPD5760	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