NPASS Compound

Structure

NPC189239 OpenBabel07101718202D 29 32 0 0 1 0 0 0 0 0999 V2000 5.8387 1.6404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6283 2.8509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2572 -3.7452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8329 -2.9054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9222 -2.6094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9429 0.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7420 -1.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7620 1.7542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5700 0.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9429 1.2693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2572 1.9550 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2572 -0.3860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6018 1.2693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2572 -2.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9222 1.2693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2875 -0.3860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6018 0.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2875 1.9550 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8026 -1.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2875 -2.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9222 0.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7620 -0.1852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9164 2.8509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8329 -1.2258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7420 -2.9054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8026 -2.9054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7620 -2.1246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5690 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 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 28 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 6 0 0 0 10 11 1 0 0 0 0 11 2 1 6 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 21 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 22 2 0 0 0 0 18 23 1 1 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	400.555
LogP:	3.673
LogD:	3.519
LogS:	-4.362
# Rotatable Bonds:	3
TPSA:	86.61
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	3.83
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
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:	-4.824
MDCK Permeability:	2.4404358555329964e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	88.9397964477539%
Volume Distribution (VD):	0.747
Pgp-substrate:	9.911174774169922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.403
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.852
CYP2D6-inhibitor:	0.127
CYP2D6-substrate:	0.758
CYP3A4-inhibitor:	0.684
CYP3A4-substrate:	0.725

ADMET: Excretion

Clearance (CL):	12.134
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.263
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.561
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.369
Carcinogencity:	0.169
Eye Corrosion:	0.003
Eye Irritation:	0.061
Respiratory Toxicity:	0.448

Download Data

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

Natural Product: NPC189239

Natural Product ID:	NPC189239
*Common Name:**	Binankadsurin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CWTKKMAJNZCARV-YRUZYCQGSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-10-6-12-7-14(25-3)20(26-4)19(24)16(12)17-13(18(23)11(10)2)8-15-21(22(17)27-5)29-9-28-15/h7-8,10-11,18,23-24H,6,9H2,1-5H3/t10-,11-,18+/m1/s1
SMILES:	C[C@@H]1Cc2cc(c(c(c2-c2c(cc3c(c2OC)OCO3)[C@H]([C@@H]1C)O)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518555
PubChem CID:	16757190
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	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
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
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	227160.0	nM	PMID[568899]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	3860.0	nM	PMID[568899]
NPT2	Others	Unspecified		Ratio	=	58.92	n.a.	PMID[568899]

☑ 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 NPC189239 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	413
0.1-0.2	1547
0.2-0.3	4144
0.3-0.4	10675
0.4-0.5	8061
0.5-0.6	4266
0.6-0.7	7673
0.7-0.8	4357
0.8-0.85	911
0.85-0.9	539
0.9-0.95	87
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC110763
1.0	High Similarity	NPC166506
1.0	High Similarity	NPC197352
0.9927	High Similarity	NPC121661
0.9927	High Similarity	NPC73467
0.9784	High Similarity	NPC252286
0.9784	High Similarity	NPC154971
0.9781	High Similarity	NPC133934
0.9781	High Similarity	NPC184641
0.9781	High Similarity	NPC229172
0.9781	High Similarity	NPC36531
0.9781	High Similarity	NPC184684
0.9781	High Similarity	NPC103637
0.9781	High Similarity	NPC230538
0.971	High Similarity	NPC324962
0.964	High Similarity	NPC239254
0.964	High Similarity	NPC172171
0.9571	High Similarity	NPC475868
0.9489	High Similarity	NPC156948
0.9489	High Similarity	NPC86605
0.9489	High Similarity	NPC46277
0.9489	High Similarity	NPC3072
0.9489	High Similarity	NPC301765
0.9489	High Similarity	NPC474039
0.9444	High Similarity	NPC475756
0.942	High Similarity	NPC290714
0.942	High Similarity	NPC201404
0.942	High Similarity	NPC53722
0.9416	High Similarity	NPC133025
0.9379	High Similarity	NPC471154
0.9371	High Similarity	NPC325720
0.9371	High Similarity	NPC316676
0.9315	High Similarity	NPC474606
0.9281	High Similarity	NPC6369
0.9281	High Similarity	NPC471183
0.9281	High Similarity	NPC30951
0.927	High Similarity	NPC289258
0.927	High Similarity	NPC56764
0.927	High Similarity	NPC145722
0.927	High Similarity	NPC555
0.927	High Similarity	NPC206737
0.927	High Similarity	NPC185680
0.927	High Similarity	NPC276026
0.927	High Similarity	NPC188378
0.927	High Similarity	NPC469659
0.927	High Similarity	NPC7515
0.927	High Similarity	NPC256776
0.9241	High Similarity	NPC473989
0.922	High Similarity	NPC41782
0.922	High Similarity	NPC191231
0.9214	High Similarity	NPC284464
0.9214	High Similarity	NPC177868
0.9203	High Similarity	NPC240279
0.9203	High Similarity	NPC180602
0.9203	High Similarity	NPC214853
0.9203	High Similarity	NPC55239
0.9189	High Similarity	NPC238834
0.9189	High Similarity	NPC476065
0.9155	High Similarity	NPC474808
0.9137	High Similarity	NPC197166
0.9137	High Similarity	NPC32189
0.9097	High Similarity	NPC474054
0.9091	High Similarity	NPC473046
0.9091	High Similarity	NPC472712
0.9091	High Similarity	NPC118385
0.9091	High Similarity	NPC187774
0.9091	High Similarity	NPC87883
0.9091	High Similarity	NPC472713
0.9067	High Similarity	NPC475592
0.9058	High Similarity	NPC471391
0.9058	High Similarity	NPC112237
0.9058	High Similarity	NPC471390
0.9058	High Similarity	NPC196937
0.9058	High Similarity	NPC58585
0.9054	High Similarity	NPC24562
0.9048	High Similarity	NPC224472
0.9028	High Similarity	NPC307466
0.9021	High Similarity	NPC469630
0.9021	High Similarity	NPC265154
0.9021	High Similarity	NPC298317
0.9021	High Similarity	NPC185071
0.9021	High Similarity	NPC218510
0.9021	High Similarity	NPC76415
0.9021	High Similarity	NPC12728
0.9021	High Similarity	NPC255566
0.9007	High Similarity	NPC9068
0.9007	High Similarity	NPC230531
0.9007	High Similarity	NPC215400
0.8993	High Similarity	NPC244983
0.8993	High Similarity	NPC312763
0.8993	High Similarity	NPC473425
0.8993	High Similarity	NPC326095
0.8993	High Similarity	NPC287745
0.8986	High Similarity	NPC175067
0.8986	High Similarity	NPC471505
0.8986	High Similarity	NPC204215
0.8986	High Similarity	NPC106739
0.898	High Similarity	NPC472709
0.898	High Similarity	NPC218041
0.898	High Similarity	NPC145979
0.898	High Similarity	NPC9933
0.898	High Similarity	NPC24425
0.898	High Similarity	NPC225815
0.898	High Similarity	NPC214326
0.898	High Similarity	NPC472710
0.898	High Similarity	NPC469707
0.898	High Similarity	NPC185955
0.898	High Similarity	NPC260781
0.898	High Similarity	NPC182368
0.898	High Similarity	NPC469706
0.8973	High Similarity	NPC304821
0.8966	High Similarity	NPC99515
0.8966	High Similarity	NPC190714
0.8966	High Similarity	NPC212890
0.8958	High Similarity	NPC326144
0.8951	High Similarity	NPC470917
0.8951	High Similarity	NPC5262
0.8951	High Similarity	NPC472714
0.8944	High Similarity	NPC216434
0.8944	High Similarity	NPC109240
0.8944	High Similarity	NPC103448
0.8929	High Similarity	NPC101624
0.8929	High Similarity	NPC256262
0.8929	High Similarity	NPC184938
0.8929	High Similarity	NPC150534
0.8926	High Similarity	NPC16791
0.8926	High Similarity	NPC77237
0.8926	High Similarity	NPC297271
0.8926	High Similarity	NPC308739
0.8926	High Similarity	NPC126405
0.8926	High Similarity	NPC217708
0.8926	High Similarity	NPC53669
0.8921	High Similarity	NPC158331
0.8913	High Similarity	NPC474017
0.8904	High Similarity	NPC39657
0.8904	High Similarity	NPC116019
0.8897	High Similarity	NPC318286
0.8897	High Similarity	NPC327651
0.8897	High Similarity	NPC180953
0.8897	High Similarity	NPC477702
0.8896	High Similarity	NPC469518
0.8896	High Similarity	NPC469475
0.8889	High Similarity	NPC81638
0.8881	High Similarity	NPC87725
0.8881	High Similarity	NPC263261
0.8881	High Similarity	NPC311530
0.8874	High Similarity	NPC473323
0.8873	High Similarity	NPC114171
0.8873	High Similarity	NPC230124
0.8873	High Similarity	NPC184613
0.8873	High Similarity	NPC6300
0.8867	High Similarity	NPC198461
0.8865	High Similarity	NPC172818
0.8865	High Similarity	NPC25695
0.8859	High Similarity	NPC21902
0.8849	High Similarity	NPC102256
0.8844	High Similarity	NPC130449
0.8844	High Similarity	NPC301961
0.8844	High Similarity	NPC166584
0.8844	High Similarity	NPC248132
0.8844	High Similarity	NPC175976
0.8841	High Similarity	NPC184814
0.8841	High Similarity	NPC126836
0.8841	High Similarity	NPC63574
0.8836	High Similarity	NPC321696
0.8836	High Similarity	NPC226540
0.8836	High Similarity	NPC321958
0.8836	High Similarity	NPC33832
0.8828	High Similarity	NPC25292
0.8828	High Similarity	NPC473045
0.8819	High Similarity	NPC474295
0.8819	High Similarity	NPC253878
0.8811	High Similarity	NPC184797
0.8811	High Similarity	NPC309124
0.8811	High Similarity	NPC160283
0.8811	High Similarity	NPC46591
0.8811	High Similarity	NPC254759
0.8803	High Similarity	NPC185908
0.8803	High Similarity	NPC283949
0.8803	High Similarity	NPC196420
0.8794	High Similarity	NPC165155
0.8794	High Similarity	NPC126409
0.8794	High Similarity	NPC34103
0.8794	High Similarity	NPC99572
0.8794	High Similarity	NPC24490
0.8794	High Similarity	NPC141765
0.8794	High Similarity	NPC142547
0.8794	High Similarity	NPC135777
0.8794	High Similarity	NPC236522
0.8786	High Similarity	NPC32778
0.8784	High Similarity	NPC55158
0.8784	High Similarity	NPC51328
0.8784	High Similarity	NPC286235
0.8784	High Similarity	NPC474393
0.8784	High Similarity	NPC474347
0.8777	High Similarity	NPC184928
0.8777	High Similarity	NPC141493
0.8768	High Similarity	NPC170844
0.8768	High Similarity	NPC212015
0.8768	High Similarity	NPC476968

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 NPC189239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	905
0.2-0.3	1970
0.3-0.4	2824
0.4-0.5	1560
0.5-0.6	914
0.6-0.7	544
0.7-0.8	82
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8768	High Similarity	NPD3027	Phase 3
0.8553	High Similarity	NPD37	Approved
0.8516	High Similarity	NPD6234	Discontinued
0.8387	Intermediate Similarity	NPD4967	Phase 2
0.8387	Intermediate Similarity	NPD4965	Approved
0.8387	Intermediate Similarity	NPD4966	Approved
0.8322	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1613	Approved
0.8261	Intermediate Similarity	NPD7228	Approved
0.8188	Intermediate Similarity	NPD3705	Approved
0.8099	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7199	Phase 2
0.8042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6674	Discontinued
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD3620	Phase 2
0.7823	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1653	Approved
0.7818	Intermediate Similarity	NPD3818	Discontinued
0.7738	Intermediate Similarity	NPD7240	Approved
0.7714	Intermediate Similarity	NPD1357	Approved
0.7671	Intermediate Similarity	NPD4908	Phase 1
0.7619	Intermediate Similarity	NPD7074	Phase 3
0.7603	Intermediate Similarity	NPD3018	Phase 2
0.7568	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7054	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7552	Intermediate Similarity	NPD1091	Approved
0.7546	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5283	Phase 1
0.7534	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1934	Approved
0.7516	Intermediate Similarity	NPD7266	Discontinued
0.7515	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2861	Phase 2
0.7469	Intermediate Similarity	NPD2978	Approved
0.7469	Intermediate Similarity	NPD2977	Approved
0.7467	Intermediate Similarity	NPD4060	Phase 1
0.7448	Intermediate Similarity	NPD2983	Phase 2
0.7448	Intermediate Similarity	NPD2982	Phase 2
0.7391	Intermediate Similarity	NPD228	Approved
0.7389	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2981	Phase 2
0.7378	Intermediate Similarity	NPD3882	Suspended
0.7378	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6797	Phase 2
0.7365	Intermediate Similarity	NPD6232	Discontinued
0.7362	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5844	Phase 1
0.7342	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7473	Discontinued
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4749	Approved
0.7329	Intermediate Similarity	NPD4005	Discontinued
0.7329	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7251	Discontinued
0.7326	Intermediate Similarity	NPD6559	Discontinued
0.7312	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7808	Phase 3
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1548	Phase 1
0.7257	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1465	Phase 2
0.7256	Intermediate Similarity	NPD2801	Approved
0.7246	Intermediate Similarity	NPD3022	Approved
0.7246	Intermediate Similarity	NPD3021	Approved
0.7229	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7680	Approved
0.7211	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5762	Approved
0.7179	Intermediate Similarity	NPD5763	Approved
0.7179	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5126	Approved
0.7172	Intermediate Similarity	NPD5125	Phase 3
0.717	Intermediate Similarity	NPD5058	Phase 3
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7143	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2238	Phase 2
0.7108	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5177	Phase 3
0.7079	Intermediate Similarity	NPD6841	Approved
0.7079	Intermediate Similarity	NPD6842	Approved
0.7079	Intermediate Similarity	NPD6843	Phase 3
0.707	Intermediate Similarity	NPD3540	Phase 1
0.7051	Intermediate Similarity	NPD4108	Discontinued
0.7041	Intermediate Similarity	NPD5494	Approved
0.7029	Intermediate Similarity	NPD7685	Pre-registration
0.7025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4055	Discovery
0.7019	Intermediate Similarity	NPD1511	Approved
0.7012	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2560	Approved
0.7006	Intermediate Similarity	NPD2563	Approved
0.7006	Intermediate Similarity	NPD3539	Phase 1
0.7006	Intermediate Similarity	NPD3817	Phase 2
0.7	Intermediate Similarity	NPD4750	Phase 3
0.7	Intermediate Similarity	NPD2677	Approved
0.7	Intermediate Similarity	NPD3094	Phase 2
0.6994	Remote Similarity	NPD3751	Discontinued
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4237	Approved
0.6981	Remote Similarity	NPD3060	Approved
0.6981	Remote Similarity	NPD4236	Phase 3
0.6977	Remote Similarity	NPD2489	Approved
0.6977	Remote Similarity	NPD27	Approved
0.6975	Remote Similarity	NPD2532	Approved
0.6975	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD2533	Approved
0.6971	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4380	Phase 2
0.6968	Remote Similarity	NPD6355	Discontinued
0.6968	Remote Similarity	NPD3657	Discovery
0.6968	Remote Similarity	NPD5735	Approved
0.6962	Remote Similarity	NPD1375	Discontinued
0.6959	Remote Similarity	NPD7229	Phase 3
0.6957	Remote Similarity	NPD7124	Phase 2
0.6954	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8455	Phase 2
0.6944	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD709	Approved
0.6933	Remote Similarity	NPD6696	Suspended
0.6933	Remote Similarity	NPD1512	Approved
0.6927	Remote Similarity	NPD4663	Approved
0.6919	Remote Similarity	NPD2970	Approved
0.6919	Remote Similarity	NPD2969	Approved
0.6914	Remote Similarity	NPD4357	Discontinued
0.6903	Remote Similarity	NPD1558	Phase 1
0.6899	Remote Similarity	NPD6099	Approved
0.6899	Remote Similarity	NPD6100	Approved
0.6883	Remote Similarity	NPD5110	Phase 2
0.6883	Remote Similarity	NPD5109	Approved
0.6883	Remote Similarity	NPD5111	Phase 2
0.6879	Remote Similarity	NPD6111	Discontinued
0.6875	Remote Similarity	NPD1652	Phase 2
0.6871	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4675	Approved
0.6867	Remote Similarity	NPD4678	Approved
0.6867	Remote Similarity	NPD7028	Phase 2
0.686	Remote Similarity	NPD3051	Approved
0.6859	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5124	Phase 1
0.6859	Remote Similarity	NPD230	Phase 1
0.6854	Remote Similarity	NPD7310	Approved
0.6854	Remote Similarity	NPD7313	Approved
0.6854	Remote Similarity	NPD4578	Approved
0.6854	Remote Similarity	NPD7312	Approved
0.6854	Remote Similarity	NPD7311	Approved
0.6854	Remote Similarity	NPD4577	Approved
0.6846	Remote Similarity	NPD3092	Approved
0.6846	Remote Similarity	NPD422	Phase 1
0.6835	Remote Similarity	NPD5588	Approved
0.6832	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4110	Phase 3
0.6832	Remote Similarity	NPD3750	Approved
0.6828	Remote Similarity	NPD7157	Approved
0.6826	Remote Similarity	NPD5090	Approved
0.6826	Remote Similarity	NPD5089	Approved
0.6824	Remote Similarity	NPD4626	Approved
0.6821	Remote Similarity	NPD8651	Approved
0.6816	Remote Similarity	NPD7309	Approved
0.6816	Remote Similarity	NPD8053	Approved
0.6816	Remote Similarity	NPD8054	Approved
0.6815	Remote Similarity	NPD4097	Suspended
0.6809	Remote Similarity	NPD2684	Approved
0.6802	Remote Similarity	NPD6959	Discontinued
0.6798	Remote Similarity	NPD7549	Discontinued
0.6796	Remote Similarity	NPD7906	Approved
0.6795	Remote Similarity	NPD4140	Approved
0.679	Remote Similarity	NPD2219	Phase 1
0.679	Remote Similarity	NPD6190	Approved
0.679	Remote Similarity	NPD5241	Discontinued
0.6786	Remote Similarity	NPD3383	Approved
0.6786	Remote Similarity	NPD3382	Approved
0.6786	Remote Similarity	NPD3384	Approved
0.6772	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4538	Approved
0.6772	Remote Similarity	NPD4536	Approved
0.6763	Remote Similarity	NPD6071	Discontinued
0.6746	Remote Similarity	NPD7819	Suspended
0.6746	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD940	Approved
0.6739	Remote Similarity	NPD846	Approved
0.6738	Remote Similarity	NPD290	Approved
0.6736	Remote Similarity	NPD7843	Approved
0.6735	Remote Similarity	NPD5536	Phase 2
0.673	Remote Similarity	NPD1510	Phase 2
0.6728	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6331	Phase 2
0.6728	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4628	Phase 3

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