NPASS Compound

Structure

NPC472768 OpenBabel07101719152D 40 44 0 0 1 0 0 0 0 0999 V2000 2.1522 -0.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2091 2.4078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0348 -1.9160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5114 -1.0905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2156 -0.1949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -0.3343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6460 -4.2694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0836 -1.1524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0050 -2.3631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0050 -0.1323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2677 -1.2477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8370 0.9323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1991 -0.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 1.9312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7891 -0.2458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6388 -1.5423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0050 -1.4099 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5582 -0.4517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4517 -0.4517 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1795 -2.8397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0368 -1.1524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1287 1.5701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9760 0.3432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5602 0.3144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5582 -1.0905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2677 -0.2945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4517 -1.0905 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6388 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5582 2.4078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6460 -2.3631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5970 -1.9235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3268 2.5025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3648 -2.4229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5602 1.2676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1795 -3.7929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 0.0249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7779 1.2756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3313 -0.2458 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 2 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 36 1 0 0 0 0 8 15 2 0 0 0 0 8 21 1 0 0 0 0 9 17 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 19 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 30 2 0 0 0 0 14 37 1 0 0 0 0 15 24 1 0 0 0 0 15 25 1 0 0 0 0 16 11 1 6 0 0 0 16 23 1 0 0 0 0 17 26 1 0 0 0 0 17 28 1 1 0 0 0 18 26 1 0 0 0 0 18 37 1 6 0 0 0 19 28 1 6 0 0 0 19 40 1 0 0 0 0 20 31 2 0 0 0 0 20 36 1 0 0 0 0 21 32 1 1 0 0 0 21 39 1 0 0 0 0 22 33 2 0 0 0 0 22 38 1 0 0 0 0 23 28 1 0 0 0 0 23 34 2 0 0 0 0 24 27 1 6 0 0 0 24 38 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 27 29 1 6 0 0 0 28 6 1 1 0 0 0 29 12 1 6 0 0 0 29 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.23
Volume:	545.595
LogP:	3.241
LogD:	1.917
LogS:	-4.448
# Rotatable Bonds:	6
TPSA:	158.8
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	6.549
Fsp3:	0.655
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.534
MDCK Permeability:	5.92E-05
Pgp-inhibitor:	0.227
Pgp-substrate:	0.896
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.192
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.763
Plasma Protein Binding (PPB):	75.12%
Volume Distribution (VD):	0.659
Pgp-substrate:	27.51%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.342
CYP3A4-substrate:	0.473

ADMET: Excretion

Clearance (CL):	8.264
Half-life (T1/2):	0.691

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.457
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.564
Carcinogencity:	0.789
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC472768

Natural Product ID:	NPC472768
*Common Name:**	RXNDRMBTLOOXAZ-ZBCNYFDBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RXNDRMBTLOOXAZ-ZBCNYFDBSA-N
Standard InCHI:	InChI=1S/C29H36O11/c1-13-16-11-27(5)24(15-8-21(32)39-25(15)35)38-22(33)12-29(13,27)40-19-10-18(37-14(2)30)26(3,4)17(9-20(31)36-7)28(19,6)23(16)34/h8,16-19,21,24,32H,1,9-12H2,2-7H3/t16-,17-,18+,19-,21-,24-,27-,28+,29-/m0/s1
SMILES:	CC(=O)OC1CC2C(C(C1(C)C)CC(=O)OC)(C(=O)C3CC4(C(OC(=O)CC4(C3=C)O2)C5=CC(OC5=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582097
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids 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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[515637]

☑ 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 NPC472768 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	259
0.1-0.2	1628
0.2-0.3	4971
0.3-0.4	8058
0.4-0.5	12843
0.5-0.6	7626
0.6-0.7	5644
0.7-0.8	1639
0.8-0.85	26
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC472769
0.9412	High Similarity	NPC472770
0.8629	High Similarity	NPC175186
0.8595	High Similarity	NPC470419
0.856	High Similarity	NPC471170
0.848	Intermediate Similarity	NPC104382
0.8468	Intermediate Similarity	NPC471357
0.8468	Intermediate Similarity	NPC117702
0.8468	Intermediate Similarity	NPC146456
0.8468	Intermediate Similarity	NPC469757
0.8413	Intermediate Similarity	NPC476855
0.84	Intermediate Similarity	NPC311534
0.8361	Intermediate Similarity	NPC470418
0.8333	Intermediate Similarity	NPC180079
0.8333	Intermediate Similarity	NPC469754
0.8333	Intermediate Similarity	NPC86159
0.8333	Intermediate Similarity	NPC251866
0.8333	Intermediate Similarity	NPC471361
0.8333	Intermediate Similarity	NPC70542
0.8333	Intermediate Similarity	NPC471352
0.8333	Intermediate Similarity	NPC476854
0.8333	Intermediate Similarity	NPC89514
0.8333	Intermediate Similarity	NPC10823
0.8333	Intermediate Similarity	NPC471360
0.8333	Intermediate Similarity	NPC469755
0.8333	Intermediate Similarity	NPC469753
0.8333	Intermediate Similarity	NPC471359
0.8333	Intermediate Similarity	NPC219085
0.8333	Intermediate Similarity	NPC197707
0.8333	Intermediate Similarity	NPC9499
0.8333	Intermediate Similarity	NPC17896
0.8333	Intermediate Similarity	NPC284406
0.8333	Intermediate Similarity	NPC470851
0.8333	Intermediate Similarity	NPC6108
0.8333	Intermediate Similarity	NPC469752
0.8333	Intermediate Similarity	NPC469751
0.8333	Intermediate Similarity	NPC471358
0.8268	Intermediate Similarity	NPC476852
0.8264	Intermediate Similarity	NPC470420
0.8254	Intermediate Similarity	NPC476859
0.825	Intermediate Similarity	NPC469794
0.825	Intermediate Similarity	NPC72772
0.8226	Intermediate Similarity	NPC27363
0.8217	Intermediate Similarity	NPC478072
0.8217	Intermediate Similarity	NPC471234
0.8189	Intermediate Similarity	NPC476851
0.8175	Intermediate Similarity	NPC179412
0.8175	Intermediate Similarity	NPC287423
0.8175	Intermediate Similarity	NPC471356
0.814	Intermediate Similarity	NPC32793
0.814	Intermediate Similarity	NPC116075
0.814	Intermediate Similarity	NPC146857
0.814	Intermediate Similarity	NPC247190
0.814	Intermediate Similarity	NPC469749
0.8136	Intermediate Similarity	NPC179642
0.813	Intermediate Similarity	NPC472004
0.8125	Intermediate Similarity	NPC476862
0.8125	Intermediate Similarity	NPC476863
0.811	Intermediate Similarity	NPC470850
0.811	Intermediate Similarity	NPC473620
0.8095	Intermediate Similarity	NPC469750
0.8095	Intermediate Similarity	NPC250556
0.8092	Intermediate Similarity	NPC59288
0.808	Intermediate Similarity	NPC469382
0.808	Intermediate Similarity	NPC204812
0.8077	Intermediate Similarity	NPC329636
0.807	Intermediate Similarity	NPC475099
0.8065	Intermediate Similarity	NPC472001
0.8062	Intermediate Similarity	NPC93416
0.8051	Intermediate Similarity	NPC474901
0.8051	Intermediate Similarity	NPC475941
0.8049	Intermediate Similarity	NPC472933
0.8047	Intermediate Similarity	NPC231529
0.8031	Intermediate Similarity	NPC240070
0.8031	Intermediate Similarity	NPC42399
0.8031	Intermediate Similarity	NPC329784
0.8016	Intermediate Similarity	NPC32868
0.8016	Intermediate Similarity	NPC86346
0.8016	Intermediate Similarity	NPC75856
0.8016	Intermediate Similarity	NPC241456
0.8016	Intermediate Similarity	NPC469379
0.8015	Intermediate Similarity	NPC194716
0.8	Intermediate Similarity	NPC88668
0.7984	Intermediate Similarity	NPC476962
0.7984	Intermediate Similarity	NPC16569
0.7984	Intermediate Similarity	NPC253456
0.7984	Intermediate Similarity	NPC173347
0.7984	Intermediate Similarity	NPC159338
0.7983	Intermediate Similarity	NPC255655
0.7983	Intermediate Similarity	NPC124053
0.7983	Intermediate Similarity	NPC42776
0.7955	Intermediate Similarity	NPC329675
0.7951	Intermediate Similarity	NPC106228
0.7951	Intermediate Similarity	NPC138372
0.7937	Intermediate Similarity	NPC471392
0.7934	Intermediate Similarity	NPC9848
0.7934	Intermediate Similarity	NPC312017
0.7923	Intermediate Similarity	NPC42670
0.7923	Intermediate Similarity	NPC471855
0.7923	Intermediate Similarity	NPC19124
0.792	Intermediate Similarity	NPC471999
0.792	Intermediate Similarity	NPC473228
0.792	Intermediate Similarity	NPC470829
0.792	Intermediate Similarity	NPC472000
0.792	Intermediate Similarity	NPC310511
0.7917	Intermediate Similarity	NPC471251
0.7907	Intermediate Similarity	NPC276838
0.7907	Intermediate Similarity	NPC232785
0.7907	Intermediate Similarity	NPC140092
0.7907	Intermediate Similarity	NPC188234
0.7907	Intermediate Similarity	NPC329986
0.7907	Intermediate Similarity	NPC91
0.7907	Intermediate Similarity	NPC125077
0.7903	Intermediate Similarity	NPC312536
0.7903	Intermediate Similarity	NPC9674
0.7903	Intermediate Similarity	NPC19028
0.7891	Intermediate Similarity	NPC298841
0.7886	Intermediate Similarity	NPC239273
0.7886	Intermediate Similarity	NPC472927
0.7886	Intermediate Similarity	NPC472934
0.7879	Intermediate Similarity	NPC171619
0.7869	Intermediate Similarity	NPC178289
0.7869	Intermediate Similarity	NPC470953
0.7863	Intermediate Similarity	NPC469674
0.7863	Intermediate Similarity	NPC225385
0.7863	Intermediate Similarity	NPC477709
0.7863	Intermediate Similarity	NPC476221
0.7863	Intermediate Similarity	NPC157817
0.7863	Intermediate Similarity	NPC298783
0.7863	Intermediate Similarity	NPC104585
0.7857	Intermediate Similarity	NPC269642
0.7857	Intermediate Similarity	NPC28532
0.7851	Intermediate Similarity	NPC475970
0.784	Intermediate Similarity	NPC151616
0.784	Intermediate Similarity	NPC109973
0.784	Intermediate Similarity	NPC48692
0.784	Intermediate Similarity	NPC470312
0.784	Intermediate Similarity	NPC281840
0.7833	Intermediate Similarity	NPC476766
0.7829	Intermediate Similarity	NPC245094
0.7829	Intermediate Similarity	NPC270109
0.7823	Intermediate Similarity	NPC113448
0.7823	Intermediate Similarity	NPC13710
0.7823	Intermediate Similarity	NPC475372
0.782	Intermediate Similarity	NPC289700
0.782	Intermediate Similarity	NPC62172
0.7815	Intermediate Similarity	NPC476765
0.7812	Intermediate Similarity	NPC47113
0.7812	Intermediate Similarity	NPC222307
0.7812	Intermediate Similarity	NPC174367
0.7805	Intermediate Similarity	NPC471816
0.7805	Intermediate Similarity	NPC266728
0.7805	Intermediate Similarity	NPC196931
0.7805	Intermediate Similarity	NPC49492
0.7805	Intermediate Similarity	NPC148458
0.7803	Intermediate Similarity	NPC248703
0.7795	Intermediate Similarity	NPC55602
0.7795	Intermediate Similarity	NPC129992
0.7795	Intermediate Similarity	NPC472399
0.7794	Intermediate Similarity	NPC5153
0.7794	Intermediate Similarity	NPC48414
0.7787	Intermediate Similarity	NPC962
0.7787	Intermediate Similarity	NPC52634
0.7786	Intermediate Similarity	NPC231240
0.7778	Intermediate Similarity	NPC202051
0.7778	Intermediate Similarity	NPC46570
0.7769	Intermediate Similarity	NPC471407
0.7769	Intermediate Similarity	NPC472928
0.7769	Intermediate Similarity	NPC473593
0.7769	Intermediate Similarity	NPC476966
0.776	Intermediate Similarity	NPC476960
0.776	Intermediate Similarity	NPC469380
0.776	Intermediate Similarity	NPC473270
0.776	Intermediate Similarity	NPC472667
0.7759	Intermediate Similarity	NPC471412
0.7752	Intermediate Similarity	NPC470882
0.7752	Intermediate Similarity	NPC473265
0.775	Intermediate Similarity	NPC475030
0.775	Intermediate Similarity	NPC471250
0.775	Intermediate Similarity	NPC273433
0.775	Intermediate Similarity	NPC476759
0.7742	Intermediate Similarity	NPC142066
0.7742	Intermediate Similarity	NPC196429
0.7742	Intermediate Similarity	NPC157376
0.7742	Intermediate Similarity	NPC309034
0.7742	Intermediate Similarity	NPC34390
0.7742	Intermediate Similarity	NPC471354
0.7742	Intermediate Similarity	NPC77319
0.7742	Intermediate Similarity	NPC471355
0.7742	Intermediate Similarity	NPC99728
0.7742	Intermediate Similarity	NPC50305
0.7742	Intermediate Similarity	NPC471353
0.7742	Intermediate Similarity	NPC87250
0.7742	Intermediate Similarity	NPC243196
0.7742	Intermediate Similarity	NPC27507
0.7742	Intermediate Similarity	NPC473656
0.7742	Intermediate Similarity	NPC471351
0.7742	Intermediate Similarity	NPC158344
0.7742	Intermediate Similarity	NPC84987
0.7742	Intermediate Similarity	NPC474483

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 NPC472768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	1924
0.2-0.3	3930
0.3-0.4	2030
0.4-0.5	572
0.5-0.6	249
0.6-0.7	155
0.7-0.8	64
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7319	Approved
0.8095	Intermediate Similarity	NPD7507	Approved
0.768	Intermediate Similarity	NPD7327	Approved
0.768	Intermediate Similarity	NPD7328	Approved
0.7619	Intermediate Similarity	NPD7516	Approved
0.7578	Intermediate Similarity	NPD6370	Approved
0.7557	Intermediate Similarity	NPD7736	Approved
0.7521	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD8380	Approved
0.75	Intermediate Similarity	NPD8379	Approved
0.75	Intermediate Similarity	NPD8378	Approved
0.75	Intermediate Similarity	NPD8296	Approved
0.7481	Intermediate Similarity	NPD8293	Discontinued
0.7462	Intermediate Similarity	NPD7492	Approved
0.7422	Intermediate Similarity	NPD8377	Approved
0.7422	Intermediate Similarity	NPD6054	Approved
0.7422	Intermediate Similarity	NPD8294	Approved
0.7419	Intermediate Similarity	NPD6882	Approved
0.7405	Intermediate Similarity	NPD6616	Approved
0.7373	Intermediate Similarity	NPD7639	Approved
0.7373	Intermediate Similarity	NPD7640	Approved
0.7364	Intermediate Similarity	NPD8033	Approved
0.7348	Intermediate Similarity	NPD7078	Approved
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7323	Intermediate Similarity	NPD7115	Discovery
0.7317	Intermediate Similarity	NPD6373	Approved
0.7317	Intermediate Similarity	NPD6372	Approved
0.7288	Intermediate Similarity	NPD7638	Approved
0.7287	Intermediate Similarity	NPD6059	Approved
0.7287	Intermediate Similarity	NPD6319	Approved
0.728	Intermediate Similarity	NPD6053	Discontinued
0.7236	Intermediate Similarity	NPD6881	Approved
0.7236	Intermediate Similarity	NPD7320	Approved
0.7236	Intermediate Similarity	NPD6899	Approved
0.7231	Intermediate Similarity	NPD6016	Approved
0.7231	Intermediate Similarity	NPD6015	Approved
0.7213	Intermediate Similarity	NPD6675	Approved
0.7213	Intermediate Similarity	NPD6008	Approved
0.7213	Intermediate Similarity	NPD7128	Approved
0.7213	Intermediate Similarity	NPD6402	Approved
0.7213	Intermediate Similarity	NPD5739	Approved
0.7176	Intermediate Similarity	NPD5988	Approved
0.7154	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.712	Intermediate Similarity	NPD6371	Approved
0.712	Intermediate Similarity	NPD7102	Approved
0.712	Intermediate Similarity	NPD6883	Approved
0.712	Intermediate Similarity	NPD7290	Approved
0.7099	Intermediate Similarity	NPD7503	Approved
0.7063	Intermediate Similarity	NPD8130	Phase 1
0.7063	Intermediate Similarity	NPD6847	Approved
0.7063	Intermediate Similarity	NPD6617	Approved
0.7063	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6009	Approved
0.704	Intermediate Similarity	NPD6013	Approved
0.704	Intermediate Similarity	NPD6014	Approved
0.704	Intermediate Similarity	NPD6012	Approved
0.7016	Intermediate Similarity	NPD5701	Approved
0.7016	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD4225	Approved
0.6992	Remote Similarity	NPD8328	Phase 3
0.6983	Remote Similarity	NPD5785	Approved
0.6967	Remote Similarity	NPD5211	Phase 2
0.696	Remote Similarity	NPD6011	Approved
0.6953	Remote Similarity	NPD4632	Approved
0.688	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5696	Approved
0.6855	Remote Similarity	NPD5141	Approved
0.685	Remote Similarity	NPD4634	Approved
0.6842	Remote Similarity	NPD8515	Approved
0.6842	Remote Similarity	NPD8517	Approved
0.6842	Remote Similarity	NPD8513	Phase 3
0.6842	Remote Similarity	NPD8516	Approved
0.6829	Remote Similarity	NPD7632	Discontinued
0.6825	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8133	Approved
0.6803	Remote Similarity	NPD4696	Approved
0.6803	Remote Similarity	NPD5285	Approved
0.6803	Remote Similarity	NPD5286	Approved
0.6797	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6033	Approved
0.6777	Remote Similarity	NPD4755	Approved
0.6777	Remote Similarity	NPD6084	Phase 2
0.6777	Remote Similarity	NPD6083	Phase 2
0.675	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7604	Phase 2
0.6719	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6274	Approved
0.6716	Remote Similarity	NPD5983	Phase 2
0.6714	Remote Similarity	NPD8338	Approved
0.6694	Remote Similarity	NPD5225	Approved
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD5224	Approved
0.6692	Remote Similarity	NPD7100	Approved
0.6692	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6642	Remote Similarity	NPD6336	Discontinued
0.6641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5175	Approved
0.664	Remote Similarity	NPD5174	Approved
0.6639	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD7637	Suspended
0.6617	Remote Similarity	NPD6335	Approved
0.6614	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5223	Approved
0.6612	Remote Similarity	NPD5210	Approved
0.6612	Remote Similarity	NPD5695	Phase 3
0.6612	Remote Similarity	NPD4629	Approved
0.661	Remote Similarity	NPD5328	Approved
0.6593	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5779	Approved
0.6583	Remote Similarity	NPD5778	Approved
0.6579	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4729	Approved
0.6562	Remote Similarity	NPD4730	Approved
0.6552	Remote Similarity	NPD5363	Approved
0.6547	Remote Similarity	NPD8337	Approved
0.6547	Remote Similarity	NPD8336	Approved
0.6541	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6317	Approved
0.6535	Remote Similarity	NPD4768	Approved
0.6535	Remote Similarity	NPD4767	Approved
0.6525	Remote Similarity	NPD6903	Approved
0.6525	Remote Similarity	NPD7260	Phase 2
0.6512	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5693	Phase 1
0.6496	Remote Similarity	NPD5786	Approved
0.6496	Remote Similarity	NPD6684	Approved
0.6496	Remote Similarity	NPD7521	Approved
0.6496	Remote Similarity	NPD6067	Discontinued
0.6496	Remote Similarity	NPD7334	Approved
0.6496	Remote Similarity	NPD5330	Approved
0.6496	Remote Similarity	NPD7146	Approved
0.6496	Remote Similarity	NPD6409	Approved
0.6493	Remote Similarity	NPD6314	Approved
0.6493	Remote Similarity	NPD6313	Approved
0.6471	Remote Similarity	NPD6909	Approved
0.6471	Remote Similarity	NPD6908	Approved
0.6462	Remote Similarity	NPD5248	Approved
0.6462	Remote Similarity	NPD5249	Phase 3
0.6462	Remote Similarity	NPD5247	Approved
0.6462	Remote Similarity	NPD5250	Approved
0.6462	Remote Similarity	NPD5251	Approved
0.6446	Remote Similarity	NPD4202	Approved
0.6446	Remote Similarity	NPD6399	Phase 3
0.6434	Remote Similarity	NPD5128	Approved
0.6423	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5222	Approved
0.6423	Remote Similarity	NPD5221	Approved
0.6423	Remote Similarity	NPD4697	Phase 3
0.641	Remote Similarity	NPD1694	Approved
0.6393	Remote Similarity	NPD6001	Approved
0.6387	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4754	Approved
0.6371	Remote Similarity	NPD5173	Approved
0.637	Remote Similarity	NPD6334	Approved
0.637	Remote Similarity	NPD6333	Approved
0.6364	Remote Similarity	NPD6411	Approved
0.6364	Remote Similarity	NPD6845	Suspended
0.6357	Remote Similarity	NPD8074	Phase 3
0.6356	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD3618	Phase 1
0.635	Remote Similarity	NPD6921	Approved
0.6349	Remote Similarity	NPD5344	Discontinued
0.6343	Remote Similarity	NPD6868	Approved
0.6333	Remote Similarity	NPD6080	Approved
0.6333	Remote Similarity	NPD6904	Approved
0.6333	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD1695	Approved
0.6333	Remote Similarity	NPD4753	Phase 2
0.6325	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3573	Approved
0.6293	Remote Similarity	NPD4269	Approved
0.6293	Remote Similarity	NPD4270	Approved
0.629	Remote Similarity	NPD7839	Suspended
0.6288	Remote Similarity	NPD5215	Approved
0.6288	Remote Similarity	NPD5216	Approved
0.6288	Remote Similarity	NPD5217	Approved
0.6281	Remote Similarity	NPD6698	Approved
0.6281	Remote Similarity	NPD46	Approved
0.6281	Remote Similarity	NPD5207	Approved
0.627	Remote Similarity	NPD6648	Approved
0.6265	Remote Similarity	NPD7799	Discontinued
0.626	Remote Similarity	NPD7748	Approved
0.626	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6672	Approved
0.624	Remote Similarity	NPD7902	Approved
0.6239	Remote Similarity	NPD5362	Discontinued
0.623	Remote Similarity	NPD7515	Phase 2
0.623	Remote Similarity	NPD5284	Approved
0.623	Remote Similarity	NPD5281	Approved
0.623	Remote Similarity	NPD6050	Approved
0.6224	Remote Similarity	NPD5956	Approved
0.6224	Remote Similarity	NPD6914	Discontinued

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