NPASS Compound

Structure

NPC471392 OpenBabel07101718292D 29 33 0 0 1 0 0 0 0 0999 V2000 3.3419 -0.4463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7615 -0.5953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9677 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4839 1.8058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7773 -2.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7239 -3.0991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0017 -1.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0393 -1.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3954 -0.6475 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5603 -1.5419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -1.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2078 -2.2610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -0.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6762 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8381 -0.4839 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 -4.1702 -2.1599 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -2.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1244 -0.5850 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 -0.8381 -0.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 18 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 21 1 0 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 28 1 0 0 0 0 11 20 1 6 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 23 2 0 0 0 0 15 19 1 0 0 0 0 15 24 2 0 0 0 0 16 25 2 0 0 0 0 16 29 1 0 0 0 0 17 20 1 1 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 6 0 0 0 19 4 1 1 0 0 0 20 21 1 1 0 0 0 21 18 1 6 0 0 0 21 27 1 0 0 0 0 22 19 1 1 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	397.272
LogP:	1.933
LogD:	1.25
LogS:	-4.62
# Rotatable Bonds:	3
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	6.82
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.355
MDCK Permeability:	1.3828534065396525e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	75.42110443115234%
Volume Distribution (VD):	0.46
Pgp-substrate:	22.4995174407959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.213
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.435

ADMET: Excretion

Clearance (CL):	4.101
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.454
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.299
Carcinogencity:	0.928
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.851

Download Data

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

Natural Product: NPC471392

Natural Product ID:	NPC471392
*Common Name:**	BIBFBLSEWSBVEL-DWRALUFWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BIBFBLSEWSBVEL-DWRALUFWSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-11-7-8-21(27)18(3)10-28-22(29-16(25)13-5-6-14(23)12(13)2)17(26)20(11,21)9-15(24)19(18,22)4/h11,17,26-27H,5-10H2,1-4H3/t11-,17-,18+,19+,20+,21+,22-/m1/s1
SMILES:	O=C(C1=C(C)C(=O)CC1)O[C@]12OC[C@]3([C@]2(C)C(=O)C[C@@]2([C@H]1O)[C@H](C)CC[C@]32O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431475
PubChem CID:	72705258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO14738	Illicium majus	Species	Schisandraceae	Eukaryota	Roots	n.a.	n.a.	PMID[24070022]
NPO14738	Illicium majus	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14738	Illicium majus	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	TC50	=	200.0	uM/ml	PMID[548003]
NPT2	Others	Unspecified		Selectivity Index	=	3.0	n.a.	PMID[548003]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	=	66700000.0	nM	PMID[548003]

☑ 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 NPC471392 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	328
0.1-0.2	1939
0.2-0.3	5539
0.3-0.4	8422
0.4-0.5	12025
0.5-0.6	6740
0.6-0.7	5539
0.7-0.8	2040
0.8-0.85	117
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8559	High Similarity	NPC138372
0.8559	High Similarity	NPC106228
0.85	High Similarity	NPC230513
0.843	Intermediate Similarity	NPC472004
0.8425	Intermediate Similarity	NPC88668
0.8347	Intermediate Similarity	NPC42673
0.8347	Intermediate Similarity	NPC9674
0.8347	Intermediate Similarity	NPC19028
0.8333	Intermediate Similarity	NPC231529
0.832	Intermediate Similarity	NPC146456
0.832	Intermediate Similarity	NPC469757
0.832	Intermediate Similarity	NPC471357
0.832	Intermediate Similarity	NPC117702
0.8306	Intermediate Similarity	NPC469790
0.8279	Intermediate Similarity	NPC154491
0.8279	Intermediate Similarity	NPC251226
0.8279	Intermediate Similarity	NPC268530
0.8264	Intermediate Similarity	NPC106644
0.8254	Intermediate Similarity	NPC311534
0.8211	Intermediate Similarity	NPC159456
0.8211	Intermediate Similarity	NPC4021
0.8189	Intermediate Similarity	NPC469754
0.8189	Intermediate Similarity	NPC469751
0.8189	Intermediate Similarity	NPC284406
0.8189	Intermediate Similarity	NPC469755
0.8189	Intermediate Similarity	NPC469753
0.8189	Intermediate Similarity	NPC180079
0.8189	Intermediate Similarity	NPC471358
0.8189	Intermediate Similarity	NPC89514
0.8189	Intermediate Similarity	NPC469752
0.8189	Intermediate Similarity	NPC471361
0.8189	Intermediate Similarity	NPC10823
0.8189	Intermediate Similarity	NPC471360
0.8189	Intermediate Similarity	NPC70542
0.8189	Intermediate Similarity	NPC86159
0.8189	Intermediate Similarity	NPC471359
0.8189	Intermediate Similarity	NPC219085
0.8189	Intermediate Similarity	NPC9499
0.8189	Intermediate Similarity	NPC251866
0.8189	Intermediate Similarity	NPC471352
0.8189	Intermediate Similarity	NPC17896
0.8189	Intermediate Similarity	NPC6108
0.8189	Intermediate Similarity	NPC197707
0.8182	Intermediate Similarity	NPC55296
0.8145	Intermediate Similarity	NPC222688
0.8145	Intermediate Similarity	NPC269642
0.813	Intermediate Similarity	NPC109973
0.8125	Intermediate Similarity	NPC473838
0.8125	Intermediate Similarity	NPC475389
0.812	Intermediate Similarity	NPC19412
0.811	Intermediate Similarity	NPC473888
0.8099	Intermediate Similarity	NPC49492
0.8099	Intermediate Similarity	NPC471816
0.8099	Intermediate Similarity	NPC266728
0.8092	Intermediate Similarity	NPC59288
0.8083	Intermediate Similarity	NPC9848
0.8083	Intermediate Similarity	NPC312017
0.808	Intermediate Similarity	NPC473979
0.808	Intermediate Similarity	NPC27363
0.8065	Intermediate Similarity	NPC310511
0.8065	Intermediate Similarity	NPC472000
0.8065	Intermediate Similarity	NPC471999
0.8062	Intermediate Similarity	NPC472769
0.8062	Intermediate Similarity	NPC180902
0.8062	Intermediate Similarity	NPC93416
0.8062	Intermediate Similarity	NPC475139
0.8049	Intermediate Similarity	NPC312536
0.8049	Intermediate Similarity	NPC475041
0.8047	Intermediate Similarity	NPC175186
0.8047	Intermediate Similarity	NPC104382
0.8047	Intermediate Similarity	NPC472770
0.8033	Intermediate Similarity	NPC13713
0.8033	Intermediate Similarity	NPC58662
0.8031	Intermediate Similarity	NPC42399
0.8031	Intermediate Similarity	NPC179412
0.8031	Intermediate Similarity	NPC287423
0.8031	Intermediate Similarity	NPC298841
0.8031	Intermediate Similarity	NPC471356
0.8017	Intermediate Similarity	NPC326542
0.8017	Intermediate Similarity	NPC178289
0.8016	Intermediate Similarity	NPC469379
0.8016	Intermediate Similarity	NPC86346
0.8016	Intermediate Similarity	NPC75856
0.8	Intermediate Similarity	NPC32793
0.8	Intermediate Similarity	NPC472002
0.8	Intermediate Similarity	NPC116075
0.8	Intermediate Similarity	NPC207251
0.8	Intermediate Similarity	NPC312833
0.8	Intermediate Similarity	NPC469749
0.8	Intermediate Similarity	NPC247190
0.8	Intermediate Similarity	NPC146857
0.7984	Intermediate Similarity	NPC159338
0.7984	Intermediate Similarity	NPC16569
0.7984	Intermediate Similarity	NPC253456
0.7984	Intermediate Similarity	NPC173347
0.7984	Intermediate Similarity	NPC143755
0.7984	Intermediate Similarity	NPC471170
0.7969	Intermediate Similarity	NPC476091
0.7969	Intermediate Similarity	NPC476078
0.7967	Intermediate Similarity	NPC475372
0.7967	Intermediate Similarity	NPC113448
0.7953	Intermediate Similarity	NPC203702
0.7953	Intermediate Similarity	NPC217901
0.7953	Intermediate Similarity	NPC293112
0.7953	Intermediate Similarity	NPC47113
0.7953	Intermediate Similarity	NPC469750
0.7953	Intermediate Similarity	NPC174367
0.7953	Intermediate Similarity	NPC250556
0.7953	Intermediate Similarity	NPC120994
0.7951	Intermediate Similarity	NPC196931
0.7951	Intermediate Similarity	NPC469794
0.7951	Intermediate Similarity	NPC72772
0.7939	Intermediate Similarity	NPC473548
0.7939	Intermediate Similarity	NPC223356
0.7939	Intermediate Similarity	NPC475154
0.7939	Intermediate Similarity	NPC471137
0.7939	Intermediate Similarity	NPC100017
0.7939	Intermediate Similarity	NPC471136
0.7939	Intermediate Similarity	NPC329636
0.7939	Intermediate Similarity	NPC475500
0.7939	Intermediate Similarity	NPC182266
0.7937	Intermediate Similarity	NPC472768
0.7937	Intermediate Similarity	NPC91693
0.7937	Intermediate Similarity	NPC11895
0.7937	Intermediate Similarity	NPC265557
0.7937	Intermediate Similarity	NPC18945
0.7937	Intermediate Similarity	NPC469382
0.7937	Intermediate Similarity	NPC105926
0.7934	Intermediate Similarity	NPC250109
0.7934	Intermediate Similarity	NPC962
0.7934	Intermediate Similarity	NPC470120
0.7923	Intermediate Similarity	NPC42670
0.7923	Intermediate Similarity	NPC471855
0.7923	Intermediate Similarity	NPC19124
0.792	Intermediate Similarity	NPC470779
0.7917	Intermediate Similarity	NPC474846
0.7917	Intermediate Similarity	NPC469656
0.7917	Intermediate Similarity	NPC94650
0.7917	Intermediate Similarity	NPC469655
0.7907	Intermediate Similarity	NPC91
0.7907	Intermediate Similarity	NPC470851
0.7907	Intermediate Similarity	NPC473593
0.7907	Intermediate Similarity	NPC162495
0.7907	Intermediate Similarity	NPC476851
0.7903	Intermediate Similarity	NPC268958
0.7903	Intermediate Similarity	NPC469380
0.7891	Intermediate Similarity	NPC329784
0.7891	Intermediate Similarity	NPC475273
0.7891	Intermediate Similarity	NPC240070
0.7891	Intermediate Similarity	NPC168849
0.7886	Intermediate Similarity	NPC284068
0.7886	Intermediate Similarity	NPC473656
0.7879	Intermediate Similarity	NPC194716
0.7879	Intermediate Similarity	NPC171619
0.7874	Intermediate Similarity	NPC476729
0.7874	Intermediate Similarity	NPC172154
0.7874	Intermediate Similarity	NPC81736
0.7874	Intermediate Similarity	NPC8369
0.7874	Intermediate Similarity	NPC24651
0.7869	Intermediate Similarity	NPC243354
0.7869	Intermediate Similarity	NPC45218
0.7869	Intermediate Similarity	NPC323821
0.7869	Intermediate Similarity	NPC299849
0.7869	Intermediate Similarity	NPC268238
0.7869	Intermediate Similarity	NPC117712
0.7869	Intermediate Similarity	NPC284915
0.7869	Intermediate Similarity	NPC143268
0.7863	Intermediate Similarity	NPC298783
0.7863	Intermediate Similarity	NPC225385
0.7863	Intermediate Similarity	NPC477709
0.7863	Intermediate Similarity	NPC168879
0.7863	Intermediate Similarity	NPC476221
0.7863	Intermediate Similarity	NPC157817
0.7863	Intermediate Similarity	NPC104585
0.7857	Intermediate Similarity	NPC170538
0.7857	Intermediate Similarity	NPC28532
0.7851	Intermediate Similarity	NPC476163
0.7851	Intermediate Similarity	NPC42658
0.7851	Intermediate Similarity	NPC473352
0.7851	Intermediate Similarity	NPC269530
0.7846	Intermediate Similarity	NPC477189
0.7846	Intermediate Similarity	NPC475314
0.7846	Intermediate Similarity	NPC476852
0.7846	Intermediate Similarity	NPC279478
0.7846	Intermediate Similarity	NPC241935
0.7846	Intermediate Similarity	NPC251564
0.7846	Intermediate Similarity	NPC475606
0.784	Intermediate Similarity	NPC142882
0.784	Intermediate Similarity	NPC112038
0.7836	Intermediate Similarity	NPC290746
0.7836	Intermediate Similarity	NPC79250
0.7833	Intermediate Similarity	NPC124053
0.7833	Intermediate Similarity	NPC179642
0.7829	Intermediate Similarity	NPC473620
0.7829	Intermediate Similarity	NPC270109
0.7829	Intermediate Similarity	NPC470850
0.7823	Intermediate Similarity	NPC204552
0.7823	Intermediate Similarity	NPC240509
0.7823	Intermediate Similarity	NPC188667
0.782	Intermediate Similarity	NPC329675

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 NPC471392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	2255
0.2-0.3	3889
0.3-0.4	1726
0.4-0.5	512
0.5-0.6	248
0.6-0.7	149
0.7-0.8	51
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8189	Intermediate Similarity	NPD7319	Approved
0.7953	Intermediate Similarity	NPD7507	Approved
0.7891	Intermediate Similarity	NPD7078	Approved
0.7874	Intermediate Similarity	NPD7492	Approved
0.784	Intermediate Similarity	NPD6059	Approved
0.784	Intermediate Similarity	NPD6054	Approved
0.7812	Intermediate Similarity	NPD6616	Approved
0.7778	Intermediate Similarity	NPD6016	Approved
0.7778	Intermediate Similarity	NPD6015	Approved
0.776	Intermediate Similarity	NPD7516	Approved
0.7752	Intermediate Similarity	NPD8293	Discontinued
0.775	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6370	Approved
0.7717	Intermediate Similarity	NPD5988	Approved
0.7692	Intermediate Similarity	NPD7736	Approved
0.768	Intermediate Similarity	NPD7327	Approved
0.768	Intermediate Similarity	NPD7328	Approved
0.7559	Intermediate Similarity	NPD6319	Approved
0.7541	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6009	Approved
0.7364	Intermediate Similarity	NPD8380	Approved
0.7364	Intermediate Similarity	NPD8379	Approved
0.7364	Intermediate Similarity	NPD8296	Approved
0.7364	Intermediate Similarity	NPD8378	Approved
0.7364	Intermediate Similarity	NPD8335	Approved
0.736	Intermediate Similarity	NPD4632	Approved
0.7355	Intermediate Similarity	NPD6008	Approved
0.7323	Intermediate Similarity	NPD7115	Discovery
0.7295	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6033	Approved
0.7287	Intermediate Similarity	NPD8294	Approved
0.7287	Intermediate Similarity	NPD8377	Approved
0.728	Intermediate Similarity	NPD6882	Approved
0.7236	Intermediate Similarity	NPD7320	Approved
0.7231	Intermediate Similarity	NPD8033	Approved
0.7213	Intermediate Similarity	NPD6675	Approved
0.7213	Intermediate Similarity	NPD7128	Approved
0.7213	Intermediate Similarity	NPD6402	Approved
0.7213	Intermediate Similarity	NPD5739	Approved
0.7177	Intermediate Similarity	NPD6373	Approved
0.7177	Intermediate Similarity	NPD6372	Approved
0.7167	Intermediate Similarity	NPD1700	Approved
0.7154	Intermediate Similarity	NPD5701	Approved
0.7154	Intermediate Similarity	NPD5697	Approved
0.7154	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.712	Intermediate Similarity	NPD4634	Approved
0.7097	Intermediate Similarity	NPD6686	Approved
0.7097	Intermediate Similarity	NPD6881	Approved
0.7097	Intermediate Similarity	NPD6899	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD7639	Approved
0.7063	Intermediate Similarity	NPD6650	Approved
0.7063	Intermediate Similarity	NPD6649	Approved
0.704	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6014	Approved
0.704	Intermediate Similarity	NPD6013	Approved
0.704	Intermediate Similarity	NPD6012	Approved
0.6992	Remote Similarity	NPD8328	Phase 3
0.6984	Remote Similarity	NPD6371	Approved
0.6984	Remote Similarity	NPD7290	Approved
0.6984	Remote Similarity	NPD7102	Approved
0.6984	Remote Similarity	NPD6883	Approved
0.697	Remote Similarity	NPD5983	Phase 2
0.697	Remote Similarity	NPD7503	Approved
0.6967	Remote Similarity	NPD7632	Discontinued
0.696	Remote Similarity	NPD6011	Approved
0.6953	Remote Similarity	NPD8133	Approved
0.6929	Remote Similarity	NPD6617	Approved
0.6929	Remote Similarity	NPD6847	Approved
0.6929	Remote Similarity	NPD8130	Phase 1
0.6929	Remote Similarity	NPD6869	Approved
0.6923	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4755	Approved
0.688	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6053	Discontinued
0.6866	Remote Similarity	NPD7604	Phase 2
0.686	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD6921	Approved
0.6829	Remote Similarity	NPD5211	Phase 2
0.6803	Remote Similarity	NPD4696	Approved
0.6803	Remote Similarity	NPD5285	Approved
0.6803	Remote Similarity	NPD4700	Approved
0.6803	Remote Similarity	NPD5286	Approved
0.6797	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6336	Discontinued
0.6741	Remote Similarity	NPD6067	Discontinued
0.672	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5141	Approved
0.6718	Remote Similarity	NPD6274	Approved
0.6716	Remote Similarity	NPD8517	Approved
0.6716	Remote Similarity	NPD8515	Approved
0.6716	Remote Similarity	NPD8516	Approved
0.6716	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8513	Phase 3
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD5224	Approved
0.6694	Remote Similarity	NPD5225	Approved
0.6691	Remote Similarity	NPD5956	Approved
0.664	Remote Similarity	NPD5174	Approved
0.664	Remote Similarity	NPD5175	Approved
0.6639	Remote Similarity	NPD6083	Phase 2
0.6639	Remote Similarity	NPD6084	Phase 2
0.6613	Remote Similarity	NPD5223	Approved
0.6612	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4202	Approved
0.6567	Remote Similarity	NPD7101	Approved
0.6567	Remote Similarity	NPD7100	Approved
0.6541	Remote Similarity	NPD6317	Approved
0.6535	Remote Similarity	NPD4768	Approved
0.6535	Remote Similarity	NPD4767	Approved
0.6508	Remote Similarity	NPD4754	Approved
0.6493	Remote Similarity	NPD6335	Approved
0.6493	Remote Similarity	NPD6314	Approved
0.6493	Remote Similarity	NPD6313	Approved
0.648	Remote Similarity	NPD5344	Discontinued
0.6479	Remote Similarity	NPD6845	Suspended
0.6479	Remote Similarity	NPD8338	Approved
0.6475	Remote Similarity	NPD8074	Phase 3
0.6475	Remote Similarity	NPD5210	Approved
0.6475	Remote Similarity	NPD5695	Phase 3
0.6475	Remote Similarity	NPD4629	Approved
0.6471	Remote Similarity	NPD5328	Approved
0.6471	Remote Similarity	NPD6909	Approved
0.6471	Remote Similarity	NPD6908	Approved
0.6457	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6399	Phase 3
0.6434	Remote Similarity	NPD5128	Approved
0.6434	Remote Similarity	NPD4729	Approved
0.6434	Remote Similarity	NPD4730	Approved
0.6423	Remote Similarity	NPD4697	Phase 3
0.6393	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD5693	Phase 1
0.6356	Remote Similarity	NPD3618	Phase 1
0.6356	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD5249	Phase 3
0.6336	Remote Similarity	NPD5247	Approved
0.6336	Remote Similarity	NPD5251	Approved
0.6336	Remote Similarity	NPD5250	Approved
0.6336	Remote Similarity	NPD5248	Approved
0.6333	Remote Similarity	NPD4753	Phase 2
0.6294	Remote Similarity	NPD7260	Phase 2
0.629	Remote Similarity	NPD5222	Approved
0.629	Remote Similarity	NPD5221	Approved
0.629	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5216	Approved
0.6288	Remote Similarity	NPD5215	Approved
0.6288	Remote Similarity	NPD5217	Approved
0.6281	Remote Similarity	NPD5785	Approved
0.6271	Remote Similarity	NPD1694	Approved
0.6265	Remote Similarity	NPD7799	Discontinued
0.626	Remote Similarity	NPD5282	Discontinued
0.6259	Remote Similarity	NPD6333	Approved
0.6259	Remote Similarity	NPD6334	Approved
0.625	Remote Similarity	NPD7625	Phase 1
0.625	Remote Similarity	NPD6903	Approved
0.624	Remote Similarity	NPD5173	Approved
0.624	Remote Similarity	NPD7902	Approved
0.623	Remote Similarity	NPD8035	Phase 2
0.623	Remote Similarity	NPD5281	Approved
0.623	Remote Similarity	NPD7637	Suspended
0.623	Remote Similarity	NPD8034	Phase 2
0.623	Remote Similarity	NPD5284	Approved
0.622	Remote Similarity	NPD4159	Approved
0.6218	Remote Similarity	NPD7334	Approved
0.6218	Remote Similarity	NPD6409	Approved
0.6218	Remote Similarity	NPD5330	Approved
0.6218	Remote Similarity	NPD7146	Approved
0.6218	Remote Similarity	NPD7521	Approved
0.6218	Remote Similarity	NPD6684	Approved
0.6212	Remote Similarity	NPD5135	Approved
0.6212	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5169	Approved
0.6197	Remote Similarity	NPD8336	Approved
0.6197	Remote Similarity	NPD8337	Approved
0.619	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD3665	Phase 1
0.6186	Remote Similarity	NPD3133	Approved
0.6165	Remote Similarity	NPD5127	Approved
0.6165	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5207	Approved
0.6148	Remote Similarity	NPD6698	Approved
0.6148	Remote Similarity	NPD46	Approved
0.6142	Remote Similarity	NPD6648	Approved
0.6129	Remote Similarity	NPD7748	Approved
0.6116	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6868	Approved
0.6098	Remote Similarity	NPD7515	Phase 2
0.6087	Remote Similarity	NPD4522	Approved
0.6066	Remote Similarity	NPD6673	Approved
0.6066	Remote Similarity	NPD6904	Approved
0.6066	Remote Similarity	NPD1695	Approved

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