NPASS Compound

Structure

NPC133025 OpenBabel07101718302D 30 32 0 0 1 0 0 0 0 0999 V2000 1.5449 -4.0508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1166 -4.0508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4143 -3.8091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4902 1.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4872 1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3409 2.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0874 2.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8503 -2.5158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7594 -1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3310 -1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 -3.1813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2436 -3.1813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8503 -1.5746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4219 -1.5746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0030 -0.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5746 -0.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1848 -0.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2436 -0.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4219 -2.5158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3375 0.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9091 0.2436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4284 -0.0000 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 3.9121 -0.1783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4837 -0.1783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2915 -2.8760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5811 1.1527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1527 1.1527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0973 1.3310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3310 1.3310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 12 2 1 6 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 2 0 0 0 0 19 26 1 1 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.2
Volume:	426.408
LogP:	3.439
LogD:	3.41
LogS:	-3.437
# Rotatable Bonds:	5
TPSA:	86.61
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	3.876
Fsp3:	0.478
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:	-4.855
MDCK Permeability:	1.841468838392757e-05
Pgp-inhibitor:	0.352
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	86.29698944091797%
Volume Distribution (VD):	0.638
Pgp-substrate:	12.713760375976562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.595
CYP3A4-inhibitor:	0.455
CYP3A4-substrate:	0.793

ADMET: Excretion

Clearance (CL):	5.154
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.381
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.515
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.776
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.6
Respiratory Toxicity:	0.684

Download Data

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

Natural Product: NPC133025

Natural Product ID:	NPC133025
*Common Name:**	Marlignan F
IUPAC Name:	n.a.
Synonyms:	Marlignan F
Standard InCHIKey:	ZSRXTAWAFTULPM-SYTFOFBDSA-N
Standard InCHI:	InChI=1S/C23H30O7/c1-11-8-13-9-15(24)20(27-4)22(29-6)17(13)18-14(19(26-3)12(11)2)10-16(25)21(28-5)23(18)30-7/h9-12,19,24-25H,8H2,1-7H3/t11-,12-,19+/m0/s1
SMILES:	CO[C@@H]1[C@@H](C)[C@@H](C)Cc2c(c3c1cc(O)c(c3OC)OC)c(OC)c(c(c2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096485
PubChem CID:	46832250
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	=	21.4	ug.mL-1	PMID[536056]
NPT27	Others	Unspecified		TI	=	15.6	n.a.	PMID[536056]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1.4	ug.mL-1	PMID[536056]

☑ 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 NPC133025 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	426
0.1-0.2	1538
0.2-0.3	4373
0.3-0.4	11997
0.4-0.5	6447
0.5-0.6	3997
0.6-0.7	7278
0.7-0.8	4946
0.8-0.85	906
0.85-0.9	537
0.9-0.95	229
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9923	High Similarity	NPC46277
0.9923	High Similarity	NPC156948
0.9923	High Similarity	NPC86605
0.9923	High Similarity	NPC301765
0.9923	High Similarity	NPC3072
0.9847	High Similarity	NPC471183
0.9845	High Similarity	NPC7515
0.9845	High Similarity	NPC289258
0.9845	High Similarity	NPC56764
0.9845	High Similarity	NPC276026
0.9845	High Similarity	NPC206737
0.9845	High Similarity	NPC469659
0.9845	High Similarity	NPC188378
0.9845	High Similarity	NPC555
0.9769	High Similarity	NPC55239
0.9769	High Similarity	NPC180602
0.9769	High Similarity	NPC214853
0.9769	High Similarity	NPC240279
0.9556	High Similarity	NPC469630
0.9485	High Similarity	NPC87883
0.9485	High Similarity	NPC121661
0.9485	High Similarity	NPC73467
0.9416	High Similarity	NPC197352
0.9416	High Similarity	NPC110763
0.9416	High Similarity	NPC189239
0.9416	High Similarity	NPC166506
0.9389	High Similarity	NPC102256
0.9385	High Similarity	NPC126836
0.9348	High Similarity	NPC474054
0.9348	High Similarity	NPC252286
0.9348	High Similarity	NPC154971
0.9338	High Similarity	NPC133934
0.9338	High Similarity	NPC184641
0.9338	High Similarity	NPC184684
0.9338	High Similarity	NPC470917
0.9323	High Similarity	NPC256262
0.9318	High Similarity	NPC32778
0.9313	High Similarity	NPC141493
0.9313	High Similarity	NPC474017
0.9313	High Similarity	NPC184928
0.9259	High Similarity	NPC184613
0.9259	High Similarity	NPC114171
0.9259	High Similarity	NPC6300
0.9259	High Similarity	NPC230124
0.9254	High Similarity	NPC202846
0.9254	High Similarity	NPC143139
0.9248	High Similarity	NPC125649
0.9248	High Similarity	NPC209199
0.9242	High Similarity	NPC175067
0.9242	High Similarity	NPC6451
0.9242	High Similarity	NPC204215
0.9231	High Similarity	NPC149008
0.9231	High Similarity	NPC207702
0.9231	High Similarity	NPC283114
0.9231	High Similarity	NPC154866
0.9225	High Similarity	NPC76451
0.9197	High Similarity	NPC229172
0.9197	High Similarity	NPC36531
0.9197	High Similarity	NPC103637
0.9197	High Similarity	NPC230538
0.9179	High Similarity	NPC158142
0.9179	High Similarity	NPC294884
0.9179	High Similarity	NPC10314
0.9179	High Similarity	NPC200557
0.9179	High Similarity	NPC69029
0.9179	High Similarity	NPC313081
0.9179	High Similarity	NPC108198
0.9173	High Similarity	NPC158331
0.9167	High Similarity	NPC45715
0.9167	High Similarity	NPC232275
0.9167	High Similarity	NPC474356
0.9167	High Similarity	NPC12275
0.916	High Similarity	NPC212015
0.916	High Similarity	NPC476968
0.916	High Similarity	NPC170844
0.9154	High Similarity	NPC169474
0.9154	High Similarity	NPC124452
0.9154	High Similarity	NPC159968
0.9154	High Similarity	NPC127587
0.9154	High Similarity	NPC236791
0.9154	High Similarity	NPC266555
0.9154	High Similarity	NPC324112
0.9154	High Similarity	NPC293054
0.9154	High Similarity	NPC82679
0.9154	High Similarity	NPC74817
0.9154	High Similarity	NPC246620
0.9154	High Similarity	NPC282000
0.9149	High Similarity	NPC474393
0.9149	High Similarity	NPC474347
0.913	High Similarity	NPC324962
0.9118	High Similarity	NPC212942
0.9118	High Similarity	NPC29868
0.9118	High Similarity	NPC79622
0.9111	High Similarity	NPC270456
0.9111	High Similarity	NPC162659
0.9111	High Similarity	NPC234952
0.9111	High Similarity	NPC265433
0.9111	High Similarity	NPC248727
0.9104	High Similarity	NPC287745
0.9104	High Similarity	NPC326095
0.9104	High Similarity	NPC160697
0.9104	High Similarity	NPC244983
0.9098	High Similarity	NPC14224
0.9098	High Similarity	NPC161958
0.9091	High Similarity	NPC192687
0.9091	High Similarity	NPC299221
0.9091	High Similarity	NPC311680
0.9091	High Similarity	NPC51840
0.9091	High Similarity	NPC234488
0.9091	High Similarity	NPC224157
0.9085	High Similarity	NPC470916
0.9084	High Similarity	NPC206615
0.9084	High Similarity	NPC28765
0.9084	High Similarity	NPC470213
0.9084	High Similarity	NPC186843
0.9084	High Similarity	NPC98631
0.9077	High Similarity	NPC223953
0.9077	High Similarity	NPC44748
0.9077	High Similarity	NPC78974
0.9077	High Similarity	NPC223136
0.9077	High Similarity	NPC18924
0.9077	High Similarity	NPC214406
0.9077	High Similarity	NPC28730
0.9077	High Similarity	NPC103823
0.9065	High Similarity	NPC239254
0.9065	High Similarity	NPC172171
0.9065	High Similarity	NPC473108
0.9051	High Similarity	NPC266650
0.9051	High Similarity	NPC308768
0.9051	High Similarity	NPC254759
0.9051	High Similarity	NPC12668
0.9051	High Similarity	NPC109240
0.9051	High Similarity	NPC309124
0.9051	High Similarity	NPC184797
0.9051	High Similarity	NPC160283
0.9044	High Similarity	NPC242715
0.9044	High Similarity	NPC22902
0.9044	High Similarity	NPC56329
0.9037	High Similarity	NPC112939
0.9037	High Similarity	NPC94750
0.9037	High Similarity	NPC47398
0.9037	High Similarity	NPC234333
0.9037	High Similarity	NPC260898
0.9037	High Similarity	NPC165155
0.9037	High Similarity	NPC99572
0.9037	High Similarity	NPC241241
0.9037	High Similarity	NPC474206
0.9037	High Similarity	NPC34103
0.9037	High Similarity	NPC470356
0.9037	High Similarity	NPC141765
0.9037	High Similarity	NPC24490
0.9037	High Similarity	NPC126409
0.9037	High Similarity	NPC121812
0.9037	High Similarity	NPC112246
0.903	High Similarity	NPC475840
0.9023	High Similarity	NPC15543
0.9021	High Similarity	NPC475756
0.9015	High Similarity	NPC190144
0.9015	High Similarity	NPC10225
0.9015	High Similarity	NPC58164
0.9008	High Similarity	NPC165045
0.9008	High Similarity	NPC118533
0.9008	High Similarity	NPC242032
0.9008	High Similarity	NPC252131
0.9	High Similarity	NPC203133
0.9	High Similarity	NPC116907
0.9	High Similarity	NPC208950
0.9	High Similarity	NPC193544
0.9	High Similarity	NPC117214
0.9	High Similarity	NPC475868
0.9	High Similarity	NPC221077
0.9	High Similarity	NPC233410
0.9	High Similarity	NPC472093
0.9	High Similarity	NPC234400
0.9	High Similarity	NPC299584
0.9	High Similarity	NPC17943
0.9	High Similarity	NPC82483
0.9	High Similarity	NPC105925
0.9	High Similarity	NPC60885
0.9	High Similarity	NPC251855
0.9	High Similarity	NPC57490
0.9	High Similarity	NPC298757
0.9	High Similarity	NPC265483
0.9	High Similarity	NPC475169
0.8986	High Similarity	NPC263261
0.8986	High Similarity	NPC87725
0.8986	High Similarity	NPC471389
0.8986	High Similarity	NPC311530
0.8986	High Similarity	NPC247291
0.8978	High Similarity	NPC25966
0.8978	High Similarity	NPC218131
0.8978	High Similarity	NPC70682
0.8978	High Similarity	NPC132804
0.8978	High Similarity	NPC105847
0.8978	High Similarity	NPC243996
0.8978	High Similarity	NPC232164
0.8978	High Similarity	NPC236306
0.8978	High Similarity	NPC53722
0.8978	High Similarity	NPC245207
0.8978	High Similarity	NPC127218

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 NPC133025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	891
0.2-0.3	1932
0.3-0.4	2778
0.4-0.5	1567
0.5-0.6	880
0.6-0.7	607
0.7-0.8	123
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.916	High Similarity	NPD3027	Phase 3
0.8676	High Similarity	NPD1613	Approved
0.8676	High Similarity	NPD1612	Clinical (unspecified phase)
0.8582	High Similarity	NPD1530	Clinical (unspecified phase)
0.8519	High Similarity	NPD1529	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD6234	Discontinued
0.8116	Intermediate Similarity	NPD4908	Phase 1
0.8043	Intermediate Similarity	NPD3018	Phase 2
0.8026	Intermediate Similarity	NPD37	Approved
0.8014	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3620	Phase 2
0.8	Intermediate Similarity	NPD5283	Phase 1
0.8	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4625	Phase 3
0.7908	Intermediate Similarity	NPD1934	Approved
0.7883	Intermediate Similarity	NPD2983	Phase 2
0.7883	Intermediate Similarity	NPD2982	Phase 2
0.7871	Intermediate Similarity	NPD4965	Approved
0.7871	Intermediate Similarity	NPD4967	Phase 2
0.7871	Intermediate Similarity	NPD4966	Approved
0.7846	Intermediate Similarity	NPD228	Approved
0.7842	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD2981	Phase 2
0.7786	Intermediate Similarity	NPD2861	Phase 2
0.7764	Intermediate Similarity	NPD7228	Approved
0.7762	Intermediate Similarity	NPD4060	Phase 1
0.7754	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD4749	Approved
0.7742	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD3705	Approved
0.7704	Intermediate Similarity	NPD1548	Phase 1
0.7703	Intermediate Similarity	NPD6674	Discontinued
0.7692	Intermediate Similarity	NPD3022	Approved
0.7692	Intermediate Similarity	NPD3021	Approved
0.7643	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2801	Approved
0.7626	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6232	Discontinued
0.7622	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4005	Discontinued
0.7593	Intermediate Similarity	NPD7473	Discontinued
0.7584	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD3882	Suspended
0.7532	Intermediate Similarity	NPD1653	Approved
0.7531	Intermediate Similarity	NPD6166	Phase 2
0.7531	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD5844	Phase 1
0.7484	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3540	Phase 1
0.7424	Intermediate Similarity	NPD4750	Phase 3
0.7403	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2238	Phase 2
0.7386	Intermediate Similarity	NPD1511	Approved
0.7383	Intermediate Similarity	NPD3539	Phase 1
0.7375	Intermediate Similarity	NPD4055	Discovery
0.7351	Intermediate Similarity	NPD5177	Phase 3
0.7349	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.732	Intermediate Similarity	NPD7124	Phase 2
0.7303	Intermediate Similarity	NPD3892	Phase 2
0.729	Intermediate Similarity	NPD1512	Approved
0.7289	Intermediate Similarity	NPD7054	Approved
0.7285	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1558	Phase 1
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD6099	Approved
0.7262	Intermediate Similarity	NPD7240	Approved
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5111	Phase 2
0.726	Intermediate Similarity	NPD5110	Phase 2
0.726	Intermediate Similarity	NPD5109	Approved
0.7255	Intermediate Similarity	NPD2677	Approved
0.725	Intermediate Similarity	NPD3817	Phase 2
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7246	Intermediate Similarity	NPD7472	Approved
0.7237	Intermediate Similarity	NPD3060	Approved
0.7234	Intermediate Similarity	NPD1091	Approved
0.723	Intermediate Similarity	NPD3657	Discovery
0.7226	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD5763	Approved
0.7215	Intermediate Similarity	NPD4678	Approved
0.7215	Intermediate Similarity	NPD4380	Phase 2
0.7215	Intermediate Similarity	NPD4675	Approved
0.7178	Intermediate Similarity	NPD5494	Approved
0.717	Intermediate Similarity	NPD5090	Approved
0.717	Intermediate Similarity	NPD5089	Approved
0.7161	Intermediate Similarity	NPD4357	Discontinued
0.7154	Intermediate Similarity	NPD846	Approved
0.7154	Intermediate Similarity	NPD940	Approved
0.7153	Intermediate Similarity	NPD3094	Phase 2
0.7152	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2219	Phase 1
0.7143	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1357	Approved
0.7135	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8053	Approved
0.7135	Intermediate Similarity	NPD8054	Approved
0.7134	Intermediate Similarity	NPD6959	Discontinued
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7114	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD5735	Approved
0.7114	Intermediate Similarity	NPD6355	Discontinued
0.7113	Intermediate Similarity	NPD422	Phase 1
0.7101	Intermediate Similarity	NPD6671	Approved
0.7101	Intermediate Similarity	NPD7157	Approved
0.7101	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6797	Phase 2
0.7092	Intermediate Similarity	NPD4626	Approved
0.709	Intermediate Similarity	NPD2684	Approved
0.7086	Intermediate Similarity	NPD1510	Phase 2
0.7083	Intermediate Similarity	NPD6696	Suspended
0.7083	Intermediate Similarity	NPD8651	Approved
0.7078	Intermediate Similarity	NPD3750	Approved
0.7077	Intermediate Similarity	NPD1242	Phase 1
0.707	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4097	Suspended
0.7063	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD2233	Approved
0.7063	Intermediate Similarity	NPD2230	Approved
0.7059	Intermediate Similarity	NPD7251	Discontinued
0.7051	Intermediate Similarity	NPD7212	Phase 2
0.7051	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7041	Phase 2
0.7051	Intermediate Similarity	NPD7213	Phase 3
0.7047	Intermediate Similarity	NPD1240	Approved
0.7037	Intermediate Similarity	NPD2563	Approved
0.7037	Intermediate Similarity	NPD2560	Approved
0.7032	Intermediate Similarity	NPD5241	Discontinued
0.702	Intermediate Similarity	NPD4538	Approved
0.702	Intermediate Similarity	NPD4536	Approved
0.702	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7808	Phase 3
0.7018	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7549	Discontinued
0.7015	Intermediate Similarity	NPD290	Approved
0.7013	Intermediate Similarity	NPD4237	Approved
0.7013	Intermediate Similarity	NPD4236	Phase 3
0.7013	Intermediate Similarity	NPD1652	Phase 2
0.7007	Intermediate Similarity	NPD7635	Approved
0.7007	Intermediate Similarity	NPD7843	Approved
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7006	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2489	Approved
0.7006	Intermediate Similarity	NPD7447	Phase 1
0.7006	Intermediate Similarity	NPD27	Approved
0.7	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD3020	Approved
0.7	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3092	Approved
0.6988	Remote Similarity	NPD7229	Phase 3
0.6988	Remote Similarity	NPD3787	Discontinued
0.698	Remote Similarity	NPD2674	Phase 3
0.6978	Remote Similarity	NPD709	Approved
0.6977	Remote Similarity	NPD4578	Approved
0.6977	Remote Similarity	NPD7312	Approved
0.6977	Remote Similarity	NPD7313	Approved
0.6977	Remote Similarity	NPD4577	Approved
0.6977	Remote Similarity	NPD7310	Approved
0.6977	Remote Similarity	NPD7311	Approved
0.6975	Remote Similarity	NPD2977	Approved
0.6975	Remote Similarity	NPD2978	Approved
0.6975	Remote Similarity	NPD7819	Suspended
0.6974	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6331	Phase 2
0.6968	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4110	Phase 3
0.6968	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1283	Approved
0.6954	Remote Similarity	NPD4663	Approved
0.6954	Remote Similarity	NPD1607	Approved
0.6951	Remote Similarity	NPD7075	Discontinued
0.6951	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1549	Phase 2
0.6946	Remote Similarity	NPD2970	Approved
0.6946	Remote Similarity	NPD2969	Approved
0.6944	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7309	Approved
0.6933	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD943	Approved
0.6928	Remote Similarity	NPD2935	Discontinued
0.6928	Remote Similarity	NPD2438	Suspended
0.6923	Remote Similarity	NPD6190	Approved
0.6918	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7906	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