NPASS Compound

Structure

NPC154971 OpenBabel07101719142D 29 33 0 0 1 0 0 0 0 0999 V2000 -1.2579 5.2934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9714 5.2934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3097 5.0441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4996 -1.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9431 3.7104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0055 2.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2238 2.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1879 0.1518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9586 0.1518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6294 4.3967 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5999 4.3967 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9431 2.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2863 2.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2457 1.5511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4750 1.5511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6294 2.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5999 2.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8512 1.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2863 3.7104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7887 0.8648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4406 0.8648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3782 1.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1648 0.4297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1830 4.0818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7508 -0.2566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1105 1.1105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3398 1.1105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2293 0.0000 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 24 1 0 0 0 0 4 25 1 0 0 0 0 5 10 1 0 0 0 0 5 12 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 27 1 0 0 0 0 8 28 1 0 0 0 0 9 26 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 1 0 0 0 10 11 1 0 0 0 0 11 2 1 1 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 21 2 0 0 0 0 14 26 1 0 0 0 0 15 20 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 18 2 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 6 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.15
Volume:	391.999
LogP:	4.41
LogD:	3.594
LogS:	-5.525
# Rotatable Bonds:	2
TPSA:	75.61
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.815
Synthetic Accessibility Score:	4.018
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:	-4.777
MDCK Permeability:	3.394389932509512e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	95.2897720336914%
Volume Distribution (VD):	0.823
Pgp-substrate:	1.7898532152175903%

ADMET: Metabolism

CYP1A2-inhibitor:	0.432
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.259
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.452
CYP2D6-substrate:	0.678
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	14.974
Half-life (T1/2):	0.089

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.15
Skin Sensitization:	0.688
Carcinogencity:	0.913
Eye Corrosion:	0.003
Eye Irritation:	0.198
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC154971

Natural Product ID:	NPC154971
*Common Name:**	Marlignan Q
IUPAC Name:	n.a.
Synonyms:	Marlignan Q
Standard InCHIKey:	QONYZAZOQAUUCL-ZHYXMNDGSA-N
Standard InCHI:	InChI=1S/C22H24O7/c1-10-5-12-6-14-21(29-9-26-14)22(25-4)16(12)17-13(19(24-3)11(10)2)7-15-20(18(17)23)28-8-27-15/h6-7,10-11,19,23H,5,8-9H2,1-4H3/t10-,11-,19+/m0/s1
SMILES:	CO[C@@H]1[C@@H](C)[C@@H](C)Cc2c(c3c1cc1OCOc1c3O)c(OC)c1c(c2)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334865
PubChem CID:	71577007
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
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20462233]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23327759]
NPO2766	Schisandra wilsoniana	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	=	22.5	ug.mL-1	PMID[500626]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	5.33	n.a.	PMID[500626]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4.22	ug.mL-1	PMID[500626]

☑ 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 NPC154971 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	423
0.1-0.2	1609
0.2-0.3	4364
0.3-0.4	11448
0.4-0.5	7176
0.5-0.6	4544
0.6-0.7	7949
0.7-0.8	3824
0.8-0.85	905
0.85-0.9	372
0.9-0.95	69
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC252286
0.9855	High Similarity	NPC121661
0.9855	High Similarity	NPC73467
0.9784	High Similarity	NPC189239
0.9784	High Similarity	NPC166506
0.9784	High Similarity	NPC110763
0.9784	High Similarity	NPC197352
0.9712	High Similarity	NPC172171
0.9712	High Similarity	NPC239254
0.971	High Similarity	NPC184684
0.971	High Similarity	NPC133934
0.971	High Similarity	NPC184641
0.9643	High Similarity	NPC475868
0.9568	High Similarity	NPC36531
0.9568	High Similarity	NPC229172
0.9568	High Similarity	NPC103637
0.9568	High Similarity	NPC230538
0.95	High Similarity	NPC324962
0.9424	High Similarity	NPC177868
0.9379	High Similarity	NPC475756
0.9353	High Similarity	NPC290714
0.9353	High Similarity	NPC53722
0.9353	High Similarity	NPC201404
0.9348	High Similarity	NPC133025
0.9348	High Similarity	NPC32189
0.9315	High Similarity	NPC471154
0.931	High Similarity	NPC473989
0.9281	High Similarity	NPC86605
0.9281	High Similarity	NPC46277
0.9281	High Similarity	NPC3072
0.9281	High Similarity	NPC301765
0.9281	High Similarity	NPC156948
0.9281	High Similarity	NPC474039
0.9252	High Similarity	NPC474606
0.9225	High Similarity	NPC474808
0.9225	High Similarity	NPC265154
0.9225	High Similarity	NPC255566
0.9225	High Similarity	NPC12728
0.9225	High Similarity	NPC298317
0.9225	High Similarity	NPC185071
0.9214	High Similarity	NPC30951
0.9214	High Similarity	NPC471183
0.9214	High Similarity	NPC9068
0.9214	High Similarity	NPC6369
0.9203	High Similarity	NPC145722
0.9203	High Similarity	NPC256776
0.9203	High Similarity	NPC188378
0.9203	High Similarity	NPC276026
0.9203	High Similarity	NPC206737
0.9203	High Similarity	NPC469659
0.9203	High Similarity	NPC555
0.9203	High Similarity	NPC7515
0.9203	High Similarity	NPC185680
0.9203	High Similarity	NPC289258
0.9203	High Similarity	NPC56764
0.9172	High Similarity	NPC325720
0.9172	High Similarity	NPC316676
0.9155	High Similarity	NPC41782
0.9155	High Similarity	NPC191231
0.9149	High Similarity	NPC284464
0.9149	High Similarity	NPC216434
0.9149	High Similarity	NPC103448
0.9137	High Similarity	NPC55239
0.9137	High Similarity	NPC214853
0.9137	High Similarity	NPC240279
0.9137	High Similarity	NPC180602
0.9128	High Similarity	NPC476065
0.9128	High Similarity	NPC238834
0.9103	High Similarity	NPC116019
0.9097	High Similarity	NPC180953
0.9097	High Similarity	NPC477702
0.9071	High Similarity	NPC197166
0.906	High Similarity	NPC312763
0.906	High Similarity	NPC198461
0.9041	High Similarity	NPC301961
0.9041	High Similarity	NPC166584
0.9034	High Similarity	NPC212890
0.9034	High Similarity	NPC33832
0.9034	High Similarity	NPC226540
0.9028	High Similarity	NPC87883
0.9021	High Similarity	NPC474295
0.9007	High Similarity	NPC475592
0.9	High Similarity	NPC126409
0.9	High Similarity	NPC142547
0.9	High Similarity	NPC24490
0.9	High Similarity	NPC165155
0.9	High Similarity	NPC99572
0.9	High Similarity	NPC34103
0.9	High Similarity	NPC141765
0.9	High Similarity	NPC150534
0.9	High Similarity	NPC135777
0.8993	High Similarity	NPC471391
0.8993	High Similarity	NPC471390
0.8986	High Similarity	NPC224472
0.8966	High Similarity	NPC307466
0.8958	High Similarity	NPC218510
0.8958	High Similarity	NPC76415
0.8958	High Similarity	NPC469630
0.8947	High Similarity	NPC230531
0.8947	High Similarity	NPC215400
0.8944	High Similarity	NPC123526
0.8944	High Similarity	NPC88640
0.8944	High Similarity	NPC193666
0.8921	High Similarity	NPC65183
0.8921	High Similarity	NPC175067
0.8921	High Similarity	NPC261812
0.8921	High Similarity	NPC204215
0.8921	High Similarity	NPC471505
0.8921	High Similarity	NPC72046
0.8919	High Similarity	NPC24425
0.8912	High Similarity	NPC71726
0.8912	High Similarity	NPC248132
0.8912	High Similarity	NPC130449
0.8904	High Similarity	NPC474054
0.8897	High Similarity	NPC473046
0.8897	High Similarity	NPC472712
0.8897	High Similarity	NPC187774
0.8897	High Similarity	NPC118385
0.8897	High Similarity	NPC472713
0.8897	High Similarity	NPC326144
0.8889	High Similarity	NPC470917
0.8881	High Similarity	NPC46591
0.8881	High Similarity	NPC109240
0.8873	High Similarity	NPC185908
0.8873	High Similarity	NPC283949
0.8867	High Similarity	NPC53669
0.8867	High Similarity	NPC126405
0.8867	High Similarity	NPC16791
0.8867	High Similarity	NPC77237
0.8867	High Similarity	NPC217708
0.8867	High Similarity	NPC297271
0.8867	High Similarity	NPC24562
0.8867	High Similarity	NPC308739
0.8857	High Similarity	NPC266848
0.8857	High Similarity	NPC112237
0.8857	High Similarity	NPC136750
0.8857	High Similarity	NPC58585
0.8857	High Similarity	NPC158331
0.8857	High Similarity	NPC196937
0.8851	High Similarity	NPC55158
0.8851	High Similarity	NPC51328
0.8851	High Similarity	NPC286235
0.8851	High Similarity	NPC85141
0.8836	High Similarity	NPC42716
0.8836	High Similarity	NPC11422
0.8836	High Similarity	NPC178014
0.8836	High Similarity	NPC318286
0.8836	High Similarity	NPC474749
0.8836	High Similarity	NPC327651
0.8828	High Similarity	NPC81638
0.8808	High Similarity	NPC473425
0.8808	High Similarity	NPC159922
0.8794	High Similarity	NPC244983
0.8794	High Similarity	NPC326095
0.8794	High Similarity	NPC287745
0.8794	High Similarity	NPC31530
0.8792	High Similarity	NPC260781
0.8792	High Similarity	NPC469706
0.8792	High Similarity	NPC469707
0.8792	High Similarity	NPC145979
0.8792	High Similarity	NPC185955
0.8792	High Similarity	NPC472709
0.8792	High Similarity	NPC225815
0.8792	High Similarity	NPC214326
0.8792	High Similarity	NPC9933
0.8792	High Similarity	NPC218041
0.8792	High Similarity	NPC182368
0.8792	High Similarity	NPC472710
0.8786	High Similarity	NPC104077
0.8786	High Similarity	NPC7744
0.8786	High Similarity	NPC106739
0.8786	High Similarity	NPC147616
0.8786	High Similarity	NPC102256
0.8786	High Similarity	NPC259742
0.8786	High Similarity	NPC219671
0.8784	High Similarity	NPC304821
0.8777	High Similarity	NPC126836
0.8777	High Similarity	NPC184814
0.8777	High Similarity	NPC63574
0.8776	High Similarity	NPC162193
0.8776	High Similarity	NPC99515
0.8776	High Similarity	NPC190714
0.8776	High Similarity	NPC321958
0.8776	High Similarity	NPC321696
0.8759	High Similarity	NPC287124
0.8759	High Similarity	NPC5262
0.8759	High Similarity	NPC472714
0.875	High Similarity	NPC226547
0.875	High Similarity	NPC56091
0.875	High Similarity	NPC254759
0.875	High Similarity	NPC309124
0.875	High Similarity	NPC184797
0.875	High Similarity	NPC160283
0.8741	High Similarity	NPC196420
0.8733	High Similarity	NPC303519
0.8732	High Similarity	NPC25333
0.8732	High Similarity	NPC256262
0.8732	High Similarity	NPC101624
0.8732	High Similarity	NPC184938
0.8732	High Similarity	NPC189474

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 NPC154971 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	933
0.2-0.3	1938
0.3-0.4	2892
0.4-0.5	1550
0.5-0.6	914
0.6-0.7	503
0.7-0.8	67
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8701	High Similarity	NPD6234	Discontinued
0.8571	High Similarity	NPD3027	Phase 3
0.8452	Intermediate Similarity	NPD4967	Phase 2
0.8452	Intermediate Similarity	NPD4965	Approved
0.8452	Intermediate Similarity	NPD4966	Approved
0.8377	Intermediate Similarity	NPD37	Approved
0.8323	Intermediate Similarity	NPD7228	Approved
0.8138	Intermediate Similarity	NPD1613	Approved
0.8138	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3705	Approved
0.8042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7199	Phase 2
0.7986	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6674	Discontinued
0.7798	Intermediate Similarity	NPD7240	Approved
0.7665	Intermediate Similarity	NPD3818	Discontinued
0.7661	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1653	Approved
0.7651	Intermediate Similarity	NPD3620	Phase 2
0.7651	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.7551	Intermediate Similarity	NPD3018	Phase 2
0.7535	Intermediate Similarity	NPD1357	Approved
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7482	Intermediate Similarity	NPD5283	Phase 1
0.7471	Intermediate Similarity	NPD7074	Phase 3
0.7469	Intermediate Similarity	NPD1934	Approved
0.745	Intermediate Similarity	NPD4625	Phase 3
0.7444	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2861	Phase 2
0.7417	Intermediate Similarity	NPD4060	Phase 1
0.7412	Intermediate Similarity	NPD7054	Approved
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2982	Phase 2
0.7397	Intermediate Similarity	NPD2983	Phase 2
0.7394	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1091	Approved
0.7368	Intermediate Similarity	NPD7472	Approved
0.7365	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7266	Discontinued
0.7338	Intermediate Similarity	NPD228	Approved
0.7333	Intermediate Similarity	NPD3882	Suspended
0.7333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2981	Phase 2
0.7321	Intermediate Similarity	NPD6232	Discontinued
0.7317	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2977	Approved
0.7317	Intermediate Similarity	NPD2978	Approved
0.7314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7473	Discontinued
0.7283	Intermediate Similarity	NPD7680	Approved
0.7279	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4749	Approved
0.7278	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6797	Phase 2
0.7222	Intermediate Similarity	NPD1548	Phase 1
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.7212	Intermediate Similarity	NPD2801	Approved
0.7209	Intermediate Similarity	NPD5844	Phase 1
0.7194	Intermediate Similarity	NPD3022	Approved
0.7194	Intermediate Similarity	NPD3021	Approved
0.7184	Intermediate Similarity	NPD7251	Discontinued
0.7184	Intermediate Similarity	NPD6559	Discontinued
0.7178	Intermediate Similarity	NPD4005	Discontinued
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6166	Phase 2
0.7135	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3540	Phase 1
0.7025	Intermediate Similarity	NPD5762	Approved
0.7025	Intermediate Similarity	NPD5763	Approved
0.7019	Intermediate Similarity	NPD5058	Phase 3
0.7018	Intermediate Similarity	NPD3787	Discontinued
0.7007	Intermediate Similarity	NPD5126	Approved
0.7007	Intermediate Similarity	NPD5125	Phase 3
0.7006	Intermediate Similarity	NPD4108	Discontinued
0.7	Intermediate Similarity	NPD5494	Approved
0.7	Intermediate Similarity	NPD3892	Phase 2
0.6982	Remote Similarity	NPD4055	Discovery
0.6981	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1511	Approved
0.697	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2238	Phase 2
0.6964	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3817	Phase 2
0.6962	Remote Similarity	NPD3539	Phase 1
0.695	Remote Similarity	NPD4750	Phase 3
0.6948	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6843	Phase 3
0.6944	Remote Similarity	NPD6842	Approved
0.6944	Remote Similarity	NPD6841	Approved
0.6937	Remote Similarity	NPD5177	Phase 3
0.6933	Remote Similarity	NPD2532	Approved
0.6933	Remote Similarity	NPD2533	Approved
0.6933	Remote Similarity	NPD2534	Approved
0.6928	Remote Similarity	NPD7028	Phase 2
0.6923	Remote Similarity	NPD3657	Discovery
0.6923	Remote Similarity	NPD5735	Approved
0.6923	Remote Similarity	NPD6355	Discontinued
0.6919	Remote Similarity	NPD7229	Phase 3
0.6918	Remote Similarity	NPD1375	Discontinued
0.6914	Remote Similarity	NPD7124	Phase 2
0.6906	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD709	Approved
0.6893	Remote Similarity	NPD7685	Pre-registration
0.689	Remote Similarity	NPD1512	Approved
0.6887	Remote Similarity	NPD6696	Suspended
0.6871	Remote Similarity	NPD4357	Discontinued
0.6864	Remote Similarity	NPD2560	Approved
0.6864	Remote Similarity	NPD2563	Approved
0.6859	Remote Similarity	NPD1558	Phase 1
0.6857	Remote Similarity	NPD3751	Discontinued
0.6855	Remote Similarity	NPD6100	Approved
0.6855	Remote Similarity	NPD6099	Approved
0.6852	Remote Similarity	NPD2677	Approved
0.6842	Remote Similarity	NPD3094	Phase 2
0.6839	Remote Similarity	NPD5111	Phase 2
0.6839	Remote Similarity	NPD5110	Phase 2
0.6839	Remote Similarity	NPD2489	Approved
0.6839	Remote Similarity	NPD27	Approved
0.6839	Remote Similarity	NPD5109	Approved
0.6836	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6111	Discontinued
0.6832	Remote Similarity	NPD3060	Approved
0.6832	Remote Similarity	NPD4237	Approved
0.6832	Remote Similarity	NPD4236	Phase 3
0.6829	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4380	Phase 2
0.6826	Remote Similarity	NPD4678	Approved
0.6826	Remote Similarity	NPD4675	Approved
0.6818	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4578	Approved
0.6816	Remote Similarity	NPD7312	Approved
0.6816	Remote Similarity	NPD7311	Approved
0.6816	Remote Similarity	NPD7310	Approved
0.6816	Remote Similarity	NPD4577	Approved
0.6816	Remote Similarity	NPD7313	Approved
0.6815	Remote Similarity	NPD230	Phase 1
0.6805	Remote Similarity	NPD8455	Phase 2
0.68	Remote Similarity	NPD422	Phase 1
0.6796	Remote Similarity	NPD4663	Approved
0.679	Remote Similarity	NPD4110	Phase 3
0.679	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3750	Approved
0.6786	Remote Similarity	NPD5089	Approved
0.6786	Remote Similarity	NPD5090	Approved
0.6782	Remote Similarity	NPD2970	Approved
0.6782	Remote Similarity	NPD2969	Approved
0.6779	Remote Similarity	NPD4626	Approved
0.6778	Remote Similarity	NPD7309	Approved
0.6778	Remote Similarity	NPD8053	Approved
0.6778	Remote Similarity	NPD8054	Approved
0.6772	Remote Similarity	NPD4097	Suspended
0.6763	Remote Similarity	NPD6959	Discontinued
0.676	Remote Similarity	NPD7549	Discontinued
0.6758	Remote Similarity	NPD7906	Approved
0.6748	Remote Similarity	NPD2219	Phase 1
0.6746	Remote Similarity	NPD3382	Approved
0.6746	Remote Similarity	NPD3384	Approved
0.6746	Remote Similarity	NPD3383	Approved
0.6728	Remote Similarity	NPD1652	Phase 2
0.6727	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3051	Approved
0.6718	Remote Similarity	NPD7827	Phase 1
0.6709	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5124	Phase 1
0.6706	Remote Similarity	NPD7819	Suspended
0.6706	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD940	Approved
0.6691	Remote Similarity	NPD846	Approved
0.6689	Remote Similarity	NPD5536	Phase 2
0.6689	Remote Similarity	NPD3092	Approved
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6331	Phase 2
0.6687	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5588	Approved
0.6686	Remote Similarity	NPD7075	Discontinued
0.6684	Remote Similarity	NPD5005	Approved
0.6684	Remote Similarity	NPD5006	Approved
0.6667	Remote Similarity	NPD7157	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD7213	Phase 3
0.6667	Remote Similarity	NPD7041	Phase 2
0.6667	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6671	Approved
0.6667	Remote Similarity	NPD7212	Phase 2
0.6667	Remote Similarity	NPD8651	Approved
0.6667	Remote Similarity	NPD7243	Clinical (unspecified phase)

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