NPASS Compound

Structure

NPC272566 OpenBabel07101718182D 29 31 0 0 1 0 0 0 0 0999 V2000 1.5420 -4.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1164 -4.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4836 1.3937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4863 1.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3403 2.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0854 2.2359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8468 -2.5110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7542 -1.3285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3285 -1.3285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1825 -3.1753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2431 -3.1753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8468 -1.5716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4211 -1.5716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9973 -0.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5716 -0.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1825 -0.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2431 -0.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4211 -2.5110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3330 0.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9074 0.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4257 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 3.9047 -0.1780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4790 -0.1780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2890 -2.8705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5762 1.1505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1505 1.1505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0972 1.3285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3285 1.3285 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 10 1 0 0 0 0 7 12 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 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 19 2 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 18 25 2 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	406.475
LogP:	3.166
LogD:	2.926
LogS:	-4.264
# Rotatable Bonds:	4
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	3.665
Fsp3:	0.409
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:	1.5743407857371494e-05
Pgp-inhibitor:	0.352
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	92.20336151123047%
Volume Distribution (VD):	0.432
Pgp-substrate:	6.008303165435791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.193
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.209
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.343
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.55
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.808

ADMET: Excretion

Clearance (CL):	4.564
Half-life (T1/2):	0.218

ADMET: Toxicity

hERG Blockers:	0.278
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.592
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.297
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.483
Respiratory Toxicity:	0.262

Download Data

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

Natural Product: NPC272566

Natural Product ID:	NPC272566
*Common Name:**	Marlignan H
IUPAC Name:	n.a.
Synonyms:	Marlignan H
Standard InCHIKey:	OCNZCMPOJIYNQT-QWRGUYRKSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-10-7-12-8-14(23)19(26-3)21(28-5)16(12)17-13(18(25)11(10)2)9-15(24)20(27-4)22(17)29-6/h8-11,23-24H,7H2,1-6H3/t10-,11-/m0/s1
SMILES:	C[C@H]1Cc2cc(c(c(c2-c2c(cc(c(c2OC)OC)O)C(=O)[C@H]1C)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094874
PubChem CID:	46832523
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	=	46.5	ug.mL-1	PMID[450639]
NPT27	Others	Unspecified		TI	=	17.6	n.a.	PMID[450639]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2.6	ug.mL-1	PMID[450639]

☑ 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 NPC272566 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	402
0.1-0.2	1533
0.2-0.3	4005
0.3-0.4	9768
0.4-0.5	8538
0.5-0.6	3174
0.6-0.7	5157
0.7-0.8	7170
0.8-0.85	2168
0.85-0.9	717
0.9-0.95	64
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC207732
0.9338	High Similarity	NPC469474
0.9329	High Similarity	NPC78505
0.9252	High Similarity	NPC165389
0.9241	High Similarity	NPC312256
0.9184	High Similarity	NPC157133
0.9178	High Similarity	NPC50954
0.9172	High Similarity	NPC110419
0.9133	High Similarity	NPC472279
0.9128	High Similarity	NPC474903
0.9116	High Similarity	NPC105213
0.9073	High Similarity	NPC220577
0.9067	High Similarity	NPC92722
0.9067	High Similarity	NPC102003
0.9048	High Similarity	NPC16353
0.9038	High Similarity	NPC469512
0.9026	High Similarity	NPC300727
0.9026	High Similarity	NPC129684
0.9026	High Similarity	NPC299520
0.9026	High Similarity	NPC199463
0.9026	High Similarity	NPC241904
0.9026	High Similarity	NPC37543
0.902	High Similarity	NPC38898
0.9007	High Similarity	NPC85131
0.9	High Similarity	NPC131451
0.9	High Similarity	NPC15329
0.9	High Similarity	NPC183655
0.9	High Similarity	NPC287395
0.8986	High Similarity	NPC142165
0.8981	High Similarity	NPC475865
0.8981	High Similarity	NPC469475
0.8981	High Similarity	NPC133065
0.8981	High Similarity	NPC469518
0.8968	High Similarity	NPC245891
0.8968	High Similarity	NPC104876
0.8968	High Similarity	NPC476242
0.8966	High Similarity	NPC470962
0.8961	High Similarity	NPC77807
0.8961	High Similarity	NPC14561
0.8961	High Similarity	NPC5379
0.8961	High Similarity	NPC274730
0.8954	High Similarity	NPC250557
0.8954	High Similarity	NPC124714
0.8954	High Similarity	NPC25127
0.8954	High Similarity	NPC287504
0.8947	High Similarity	NPC19980
0.8947	High Similarity	NPC45291
0.894	High Similarity	NPC195763
0.894	High Similarity	NPC69430
0.894	High Similarity	NPC142876
0.894	High Similarity	NPC40290
0.894	High Similarity	NPC264550
0.894	High Similarity	NPC139293
0.894	High Similarity	NPC333691
0.894	High Similarity	NPC264289
0.894	High Similarity	NPC200060
0.8933	High Similarity	NPC119660
0.8933	High Similarity	NPC77598
0.8933	High Similarity	NPC93034
0.8924	High Similarity	NPC39306
0.8919	High Similarity	NPC119663
0.8919	High Similarity	NPC471417
0.8919	High Similarity	NPC287722
0.8919	High Similarity	NPC254659
0.8917	High Similarity	NPC42797
0.8917	High Similarity	NPC473445
0.891	High Similarity	NPC24627
0.891	High Similarity	NPC228785
0.891	High Similarity	NPC84571
0.891	High Similarity	NPC14353
0.891	High Similarity	NPC56085
0.8903	High Similarity	NPC469584
0.8903	High Similarity	NPC472963
0.8903	High Similarity	NPC178976
0.8896	High Similarity	NPC472048
0.8896	High Similarity	NPC134287
0.8896	High Similarity	NPC31018
0.8896	High Similarity	NPC255807
0.8896	High Similarity	NPC130589
0.8889	High Similarity	NPC121522
0.8889	High Similarity	NPC181209
0.8889	High Similarity	NPC35763
0.8889	High Similarity	NPC312338
0.8889	High Similarity	NPC149889
0.8889	High Similarity	NPC100971
0.8889	High Similarity	NPC291802
0.8889	High Similarity	NPC245382
0.8889	High Similarity	NPC60972
0.8889	High Similarity	NPC269451
0.8889	High Similarity	NPC209487
0.8889	High Similarity	NPC39732
0.8889	High Similarity	NPC216769
0.8889	High Similarity	NPC100263
0.8889	High Similarity	NPC131266
0.8889	High Similarity	NPC474993
0.8889	High Similarity	NPC208760
0.8882	High Similarity	NPC469506
0.8882	High Similarity	NPC151473
0.8882	High Similarity	NPC178737
0.8882	High Similarity	NPC225854
0.8882	High Similarity	NPC239363
0.8874	High Similarity	NPC254702
0.8874	High Similarity	NPC139364
0.8874	High Similarity	NPC194653
0.8874	High Similarity	NPC80710
0.8874	High Similarity	NPC203747
0.8867	High Similarity	NPC138978
0.8861	High Similarity	NPC291977
0.8861	High Similarity	NPC270837
0.8859	High Similarity	NPC275278
0.8854	High Similarity	NPC278052
0.8854	High Similarity	NPC40491
0.8854	High Similarity	NPC61010
0.8854	High Similarity	NPC311740
0.8851	High Similarity	NPC301178
0.8851	High Similarity	NPC284556
0.8851	High Similarity	NPC18714
0.8851	High Similarity	NPC49108
0.8846	High Similarity	NPC37502
0.8846	High Similarity	NPC40702
0.8846	High Similarity	NPC267627
0.8846	High Similarity	NPC100123
0.8846	High Similarity	NPC45846
0.8844	High Similarity	NPC19158
0.8839	High Similarity	NPC472907
0.8839	High Similarity	NPC474167
0.8839	High Similarity	NPC470762
0.8839	High Similarity	NPC54928
0.8831	High Similarity	NPC107109
0.8831	High Similarity	NPC89474
0.8831	High Similarity	NPC93552
0.8831	High Similarity	NPC472905
0.8831	High Similarity	NPC303950
0.8831	High Similarity	NPC469550
0.8828	High Similarity	NPC471182
0.8824	High Similarity	NPC151425
0.8824	High Similarity	NPC256406
0.8824	High Similarity	NPC262623
0.8819	High Similarity	NPC188378
0.8819	High Similarity	NPC555
0.8819	High Similarity	NPC206737
0.8819	High Similarity	NPC469659
0.8819	High Similarity	NPC289258
0.8819	High Similarity	NPC7515
0.8819	High Similarity	NPC56764
0.8819	High Similarity	NPC276026
0.8816	High Similarity	NPC48479
0.8816	High Similarity	NPC177298
0.8808	High Similarity	NPC188074
0.8808	High Similarity	NPC125449
0.8797	High Similarity	NPC312056
0.8797	High Similarity	NPC294965
0.8797	High Similarity	NPC472964
0.8797	High Similarity	NPC149389
0.8797	High Similarity	NPC84515
0.8792	High Similarity	NPC46161
0.8792	High Similarity	NPC239608
0.879	High Similarity	NPC155302
0.879	High Similarity	NPC200746
0.879	High Similarity	NPC320359
0.879	High Similarity	NPC161947
0.879	High Similarity	NPC36217
0.879	High Similarity	NPC474960
0.879	High Similarity	NPC472902
0.8782	High Similarity	NPC181960
0.8782	High Similarity	NPC472910
0.8782	High Similarity	NPC245758
0.8782	High Similarity	NPC222814
0.8782	High Similarity	NPC262286
0.8782	High Similarity	NPC36852
0.8782	High Similarity	NPC96167
0.8782	High Similarity	NPC472911
0.8782	High Similarity	NPC165977
0.8782	High Similarity	NPC472914
0.8782	High Similarity	NPC472913
0.8782	High Similarity	NPC474990
0.8782	High Similarity	NPC217677
0.8782	High Similarity	NPC136674
0.8782	High Similarity	NPC78103
0.8782	High Similarity	NPC247713
0.8782	High Similarity	NPC179732
0.8774	High Similarity	NPC16082
0.8774	High Similarity	NPC168247
0.8774	High Similarity	NPC82592
0.8774	High Similarity	NPC208197
0.8774	High Similarity	NPC57674
0.8774	High Similarity	NPC152951
0.8774	High Similarity	NPC20830
0.8774	High Similarity	NPC230149
0.8774	High Similarity	NPC39184
0.8774	High Similarity	NPC256612
0.8774	High Similarity	NPC117992
0.8774	High Similarity	NPC234485
0.8774	High Similarity	NPC79998
0.8774	High Similarity	NPC67396
0.8766	High Similarity	NPC260979
0.8766	High Similarity	NPC472912
0.8766	High Similarity	NPC477231
0.8766	High Similarity	NPC471982
0.8766	High Similarity	NPC180944

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 NPC272566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	938
0.2-0.3	1712
0.3-0.4	2695
0.4-0.5	1781
0.5-0.6	1011
0.6-0.7	484
0.7-0.8	138
0.8-0.85	20
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD2801	Approved
0.8645	High Similarity	NPD1934	Approved
0.8634	High Similarity	NPD7473	Discontinued
0.8599	High Similarity	NPD3882	Suspended
0.859	High Similarity	NPD1465	Phase 2
0.8562	High Similarity	NPD6232	Discontinued
0.8481	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD1511	Approved
0.8258	Intermediate Similarity	NPD1512	Approved
0.8242	Intermediate Similarity	NPD3818	Discontinued
0.8232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6166	Phase 2
0.8232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD943	Approved
0.8176	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD230	Phase 1
0.8098	Intermediate Similarity	NPD5494	Approved
0.8079	Intermediate Similarity	NPD1510	Phase 2
0.8075	Intermediate Similarity	NPD3817	Phase 2
0.8067	Intermediate Similarity	NPD1607	Approved
0.805	Intermediate Similarity	NPD4380	Phase 2
0.8037	Intermediate Similarity	NPD6234	Discontinued
0.8036	Intermediate Similarity	NPD7074	Phase 3
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7054	Approved
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3027	Phase 3
0.7962	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD37	Approved
0.7935	Intermediate Similarity	NPD3750	Approved
0.7929	Intermediate Similarity	NPD7472	Approved
0.7901	Intermediate Similarity	NPD7819	Suspended
0.7848	Intermediate Similarity	NPD2533	Approved
0.7848	Intermediate Similarity	NPD2532	Approved
0.7848	Intermediate Similarity	NPD2534	Approved
0.7844	Intermediate Similarity	NPD3926	Phase 2
0.7838	Intermediate Similarity	NPD9494	Approved
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7808	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1549	Phase 2
0.7805	Intermediate Similarity	NPD4965	Approved
0.7805	Intermediate Similarity	NPD4966	Approved
0.7805	Intermediate Similarity	NPD4967	Phase 2
0.7791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7758	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7075	Discontinued
0.7742	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7251	Discontinued
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7199	Phase 2
0.7718	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6599	Discontinued
0.7706	Intermediate Similarity	NPD7228	Approved
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7683	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2796	Approved
0.7677	Intermediate Similarity	NPD6100	Approved
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7677	Intermediate Similarity	NPD6099	Approved
0.7667	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3749	Approved
0.7636	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1247	Approved
0.7619	Intermediate Similarity	NPD9269	Phase 2
0.7613	Intermediate Similarity	NPD3748	Approved
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7582	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1613	Approved
0.7562	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.7532	Intermediate Similarity	NPD2800	Approved
0.7529	Intermediate Similarity	NPD5242	Approved
0.7516	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.7484	Intermediate Similarity	NPD6651	Approved
0.7455	Intermediate Similarity	NPD7411	Suspended
0.7451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6190	Approved
0.7429	Intermediate Similarity	NPD7685	Pre-registration
0.7429	Intermediate Similarity	NPD6559	Discontinued
0.7425	Intermediate Similarity	NPD5353	Approved
0.7425	Intermediate Similarity	NPD5402	Approved
0.7421	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD447	Suspended
0.7405	Intermediate Similarity	NPD2344	Approved
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7768	Phase 2
0.7375	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9268	Approved
0.7346	Intermediate Similarity	NPD4357	Discontinued
0.7333	Intermediate Similarity	NPD3226	Approved
0.7329	Intermediate Similarity	NPD5536	Phase 2
0.7285	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD3972	Approved
0.7267	Intermediate Similarity	NPD5710	Approved
0.7255	Intermediate Similarity	NPD3018	Phase 2
0.7253	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6385	Approved
0.7246	Intermediate Similarity	NPD6386	Approved
0.7233	Intermediate Similarity	NPD1551	Phase 2
0.7232	Intermediate Similarity	NPD7240	Approved
0.7229	Intermediate Similarity	NPD7458	Discontinued
0.7226	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD2309	Approved
0.7219	Intermediate Similarity	NPD5978	Approved
0.7219	Intermediate Similarity	NPD5977	Approved
0.7212	Intermediate Similarity	NPD920	Approved
0.7212	Intermediate Similarity	NPD5403	Approved
0.7208	Intermediate Similarity	NPD4908	Phase 1
0.7207	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1243	Approved
0.719	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD2346	Discontinued
0.7172	Intermediate Similarity	NPD5283	Phase 1
0.7171	Intermediate Similarity	NPD1283	Approved
0.7169	Intermediate Similarity	NPD1653	Approved
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD5089	Approved
0.7143	Intermediate Similarity	NPD5090	Approved
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1470	Approved
0.7115	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1651	Approved
0.7105	Intermediate Similarity	NPD2983	Phase 2
0.7105	Intermediate Similarity	NPD2982	Phase 2
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5401	Approved
0.7091	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1610	Phase 2
0.7079	Intermediate Similarity	NPD5953	Discontinued
0.7062	Intermediate Similarity	NPD7286	Phase 2
0.7056	Intermediate Similarity	NPD8312	Approved
0.7056	Intermediate Similarity	NPD8313	Approved
0.7056	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7039	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2981	Phase 2
0.7034	Intermediate Similarity	NPD228	Approved
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.7025	Intermediate Similarity	NPD3620	Phase 2
0.7025	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5405	Approved
0.7019	Intermediate Similarity	NPD5404	Approved
0.7019	Intermediate Similarity	NPD5406	Approved
0.7019	Intermediate Similarity	NPD5408	Approved
0.7018	Intermediate Similarity	NPD4288	Approved
0.7013	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2654	Approved
0.6993	Remote Similarity	NPD4749	Approved
0.6993	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2403	Approved
0.6984	Remote Similarity	NPD6779	Approved
0.6984	Remote Similarity	NPD6781	Approved
0.6984	Remote Similarity	NPD6776	Approved
0.6984	Remote Similarity	NPD6777	Approved
0.6984	Remote Similarity	NPD6782	Approved
0.6984	Remote Similarity	NPD6780	Approved
0.6984	Remote Similarity	NPD6778	Approved
0.6981	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD1933	Approved
0.6975	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1201	Approved
0.6974	Remote Similarity	NPD1281	Approved
0.697	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD17	Approved
0.6946	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD9545	Approved
0.6931	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD824	Approved
0.6918	Remote Similarity	NPD2979	Phase 3
0.6914	Remote Similarity	NPD8127	Discontinued
0.6914	Remote Similarity	NPD2438	Suspended

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