NPASS Compound

Structure

NPC11956 OpenBabel07101718312D 31 33 0 0 1 0 0 0 0 0999 V2000 -0.8406 -3.3971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5217 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5217 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7139 0.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4853 0.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -3.3971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -1.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4644 -0.0502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7781 -0.7365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7497 -1.2075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1562 0.3094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5217 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6811 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4019 -0.3014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.4559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7190 -1.1567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -1.4559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8406 -0.4853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8406 -0.4853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.9412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3622 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3298 -1.9110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.6811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9702 -0.2192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6811 -1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6811 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 22 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 2 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 23 1 0 0 0 0 15 25 2 0 0 0 0 15 30 1 0 0 0 0 16 26 2 0 0 0 0 16 31 1 0 0 0 0 18 22 1 1 0 0 0 18 23 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 1 0 0 0 20 30 1 0 0 0 0 21 24 1 6 0 0 0 21 31 1 0 0 0 0 22 24 1 6 0 0 0 23 5 1 1 0 0 0 24 6 1 1 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.21
Volume:	443.704
LogP:	2.412
LogD:	1.631
LogS:	-4.16
# Rotatable Bonds:	6
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	5.154
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.888
MDCK Permeability:	2.0245490304660052e-05
Pgp-inhibitor:	0.189
Pgp-substrate:	0.435
Human Intestinal Absorption (HIA):	0.828
20% Bioavailability (F20%):	0.407
30% Bioavailability (F30%):	0.874

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.924
Plasma Protein Binding (PPB):	87.39911651611328%
Volume Distribution (VD):	1.131
Pgp-substrate:	17.135000228881836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.267
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.487
CYP2D6-inhibitor:	0.531
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	3.492
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.725
Drug-inuced Liver Injury (DILI):	0.569
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.406
Carcinogencity:	0.223
Eye Corrosion:	0.017
Eye Irritation:	0.076
Respiratory Toxicity:	0.224

Download Data

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

Natural Product: NPC11956

Natural Product ID:	NPC11956
*Common Name:**	VQWPROISONEVNZ-GIOJCLGXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VQWPROISONEVNZ-GIOJCLGXSA-N
Standard InCHI:	InChI=1S/C24H32O7/c1-14-8-7-9-18-22(4,11-10-17-12-19(27)29-13-17)24(6,28)21(31-16(3)26)20(23(14,18)5)30-15(2)25/h8,10-12,18,20-21,28H,7,9,13H2,1-6H3/b11-10+/t18-,20+,21+,22-,23+,24+/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H](OC(=O)C)[C@@]2(C)C(=CCC[C@@H]2[C@@]([C@@]1(C)O)(C)/C=C/C1=CC(=O)OC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577093
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	<	50.0	%	PMID[511533]

☑ 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 NPC11956 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	199
0.1-0.2	1136
0.2-0.3	3771
0.3-0.4	6050
0.4-0.5	14657
0.5-0.6	9084
0.6-0.7	6023
0.7-0.8	1641
0.8-0.85	121
0.85-0.9	11
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC23584
0.9479	High Similarity	NPC472554
0.9381	High Similarity	NPC472552
0.9109	High Similarity	NPC50124
0.91	High Similarity	NPC471206
0.898	High Similarity	NPC38855
0.8932	High Similarity	NPC177047
0.8763	High Similarity	NPC276110
0.8713	High Similarity	NPC45897
0.8687	High Similarity	NPC278673
0.8687	High Similarity	NPC475068
0.8586	High Similarity	NPC120446
0.8586	High Similarity	NPC205143
0.8585	High Similarity	NPC317460
0.8585	High Similarity	NPC328074
0.8585	High Similarity	NPC321272
0.8585	High Similarity	NPC470025
0.8571	High Similarity	NPC316708
0.8558	High Similarity	NPC38948
0.8557	High Similarity	NPC7349
0.8544	High Similarity	NPC51719
0.8515	High Similarity	NPC475617
0.8515	High Similarity	NPC11974
0.8511	High Similarity	NPC471219
0.8505	High Similarity	NPC470027
0.8491	Intermediate Similarity	NPC470026
0.8491	Intermediate Similarity	NPC17791
0.8485	Intermediate Similarity	NPC473153
0.8476	Intermediate Similarity	NPC206618
0.8476	Intermediate Similarity	NPC316974
0.8469	Intermediate Similarity	NPC469491
0.8469	Intermediate Similarity	NPC105490
0.8462	Intermediate Similarity	NPC187435
0.8462	Intermediate Similarity	NPC67321
0.8462	Intermediate Similarity	NPC122816
0.8462	Intermediate Similarity	NPC471205
0.8438	Intermediate Similarity	NPC246028
0.8438	Intermediate Similarity	NPC82876
0.8416	Intermediate Similarity	NPC188968
0.84	Intermediate Similarity	NPC473244
0.84	Intermediate Similarity	NPC51499
0.8381	Intermediate Similarity	NPC306265
0.8381	Intermediate Similarity	NPC311223
0.8381	Intermediate Similarity	NPC48548
0.8381	Intermediate Similarity	NPC128795
0.8381	Intermediate Similarity	NPC135015
0.8381	Intermediate Similarity	NPC181994
0.8381	Intermediate Similarity	NPC217921
0.8367	Intermediate Similarity	NPC205034
0.8367	Intermediate Similarity	NPC53555
0.8367	Intermediate Similarity	NPC162615
0.8367	Intermediate Similarity	NPC110022
0.8367	Intermediate Similarity	NPC152778
0.8351	Intermediate Similarity	NPC78973
0.835	Intermediate Similarity	NPC474124
0.835	Intermediate Similarity	NPC474575
0.835	Intermediate Similarity	NPC281378
0.835	Intermediate Similarity	NPC120009
0.8333	Intermediate Similarity	NPC471204
0.8317	Intermediate Similarity	NPC275086
0.8317	Intermediate Similarity	NPC325229
0.8302	Intermediate Similarity	NPC475586
0.8302	Intermediate Similarity	NPC40728
0.83	Intermediate Similarity	NPC471765
0.83	Intermediate Similarity	NPC16967
0.83	Intermediate Similarity	NPC211810
0.83	Intermediate Similarity	NPC165632
0.83	Intermediate Similarity	NPC284194
0.83	Intermediate Similarity	NPC57664
0.83	Intermediate Similarity	NPC129569
0.83	Intermediate Similarity	NPC221801
0.8286	Intermediate Similarity	NPC109376
0.8286	Intermediate Similarity	NPC473586
0.8286	Intermediate Similarity	NPC302788
0.8286	Intermediate Similarity	NPC88013
0.8286	Intermediate Similarity	NPC125423
0.8286	Intermediate Similarity	NPC475074
0.8269	Intermediate Similarity	NPC473543
0.8252	Intermediate Similarity	NPC475344
0.8252	Intermediate Similarity	NPC472815
0.8252	Intermediate Similarity	NPC476081
0.8252	Intermediate Similarity	NPC476471
0.8247	Intermediate Similarity	NPC20946
0.8235	Intermediate Similarity	NPC254567
0.8235	Intermediate Similarity	NPC474571
0.8235	Intermediate Similarity	NPC79303
0.8235	Intermediate Similarity	NPC473510
0.8235	Intermediate Similarity	NPC271295
0.8229	Intermediate Similarity	NPC131329
0.8224	Intermediate Similarity	NPC119550
0.8218	Intermediate Similarity	NPC199099
0.8218	Intermediate Similarity	NPC210337
0.8208	Intermediate Similarity	NPC475263
0.8208	Intermediate Similarity	NPC318363
0.8208	Intermediate Similarity	NPC475418
0.8208	Intermediate Similarity	NPC224660
0.8208	Intermediate Similarity	NPC470024
0.8208	Intermediate Similarity	NPC473482
0.8198	Intermediate Similarity	NPC284707
0.8191	Intermediate Similarity	NPC49208
0.819	Intermediate Similarity	NPC172867
0.819	Intermediate Similarity	NPC88349
0.819	Intermediate Similarity	NPC82251
0.819	Intermediate Similarity	NPC477125
0.819	Intermediate Similarity	NPC34768
0.819	Intermediate Similarity	NPC186668
0.8173	Intermediate Similarity	NPC120321
0.8173	Intermediate Similarity	NPC474822
0.8173	Intermediate Similarity	NPC187302
0.8173	Intermediate Similarity	NPC473523
0.8173	Intermediate Similarity	NPC189588
0.8173	Intermediate Similarity	NPC134270
0.8173	Intermediate Similarity	NPC97487
0.8173	Intermediate Similarity	NPC196471
0.8173	Intermediate Similarity	NPC10232
0.8165	Intermediate Similarity	NPC469496
0.8165	Intermediate Similarity	NPC469454
0.8165	Intermediate Similarity	NPC469463
0.8163	Intermediate Similarity	NPC310479
0.8163	Intermediate Similarity	NPC221111
0.8163	Intermediate Similarity	NPC280149
0.8148	Intermediate Similarity	NPC179798
0.8148	Intermediate Similarity	NPC304180
0.8148	Intermediate Similarity	NPC470076
0.8137	Intermediate Similarity	NPC65700
0.8131	Intermediate Similarity	NPC475065
0.8131	Intermediate Similarity	NPC472216
0.8131	Intermediate Similarity	NPC284828
0.8131	Intermediate Similarity	NPC173905
0.8131	Intermediate Similarity	NPC5475
0.8125	Intermediate Similarity	NPC131813
0.8119	Intermediate Similarity	NPC88009
0.8119	Intermediate Similarity	NPC472995
0.8113	Intermediate Similarity	NPC330011
0.8113	Intermediate Similarity	NPC179380
0.8113	Intermediate Similarity	NPC329048
0.8108	Intermediate Similarity	NPC53396
0.8108	Intermediate Similarity	NPC98249
0.81	Intermediate Similarity	NPC472416
0.81	Intermediate Similarity	NPC105375
0.81	Intermediate Similarity	NPC140277
0.81	Intermediate Similarity	NPC191521
0.81	Intermediate Similarity	NPC182826
0.81	Intermediate Similarity	NPC472360
0.8095	Intermediate Similarity	NPC264867
0.8095	Intermediate Similarity	NPC470321
0.8095	Intermediate Similarity	NPC473207
0.8095	Intermediate Similarity	NPC81567
0.8095	Intermediate Similarity	NPC201880
0.8085	Intermediate Similarity	NPC471218
0.8081	Intermediate Similarity	NPC477574
0.8077	Intermediate Similarity	NPC475038
0.8077	Intermediate Similarity	NPC471363
0.8077	Intermediate Similarity	NPC238397
0.8077	Intermediate Similarity	NPC109195
0.8077	Intermediate Similarity	NPC295791
0.8077	Intermediate Similarity	NPC470972
0.8073	Intermediate Similarity	NPC470063
0.8073	Intermediate Similarity	NPC476801
0.8061	Intermediate Similarity	NPC261320
0.8061	Intermediate Similarity	NPC314727
0.8058	Intermediate Similarity	NPC471413
0.8058	Intermediate Similarity	NPC230546
0.8058	Intermediate Similarity	NPC16601
0.8058	Intermediate Similarity	NPC474190
0.8058	Intermediate Similarity	NPC272223
0.8058	Intermediate Similarity	NPC324841
0.8056	Intermediate Similarity	NPC472215
0.8056	Intermediate Similarity	NPC472214
0.8053	Intermediate Similarity	NPC112936
0.8053	Intermediate Similarity	NPC475885
0.8041	Intermediate Similarity	NPC473891
0.8041	Intermediate Similarity	NPC245004
0.8039	Intermediate Similarity	NPC99726
0.8021	Intermediate Similarity	NPC35933
0.802	Intermediate Similarity	NPC472189
0.802	Intermediate Similarity	NPC471372
0.802	Intermediate Similarity	NPC471362
0.802	Intermediate Similarity	NPC8774
0.8019	Intermediate Similarity	NPC252296
0.8019	Intermediate Similarity	NPC218158
0.8019	Intermediate Similarity	NPC119855
0.8019	Intermediate Similarity	NPC239961
0.8019	Intermediate Similarity	NPC111952
0.8019	Intermediate Similarity	NPC220217
0.8018	Intermediate Similarity	NPC471816
0.8	Intermediate Similarity	NPC7613
0.8	Intermediate Similarity	NPC159533
0.8	Intermediate Similarity	NPC7644
0.8	Intermediate Similarity	NPC476848
0.8	Intermediate Similarity	NPC127933
0.8	Intermediate Similarity	NPC23748
0.8	Intermediate Similarity	NPC472821
0.8	Intermediate Similarity	NPC475889
0.8	Intermediate Similarity	NPC56448
0.7982	Intermediate Similarity	NPC233500
0.7982	Intermediate Similarity	NPC324683
0.7981	Intermediate Similarity	NPC235920
0.7981	Intermediate Similarity	NPC25177
0.7981	Intermediate Similarity	NPC268829

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 NPC11956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1301
0.2-0.3	3563
0.3-0.4	2512
0.4-0.5	1119
0.5-0.6	307
0.6-0.7	159
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD6648	Approved
0.8155	Intermediate Similarity	NPD5344	Discontinued
0.7963	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7516	Approved
0.7788	Intermediate Similarity	NPD4225	Approved
0.7788	Intermediate Similarity	NPD7638	Approved
0.7727	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7327	Approved
0.7719	Intermediate Similarity	NPD7328	Approved
0.7714	Intermediate Similarity	NPD7640	Approved
0.7714	Intermediate Similarity	NPD7639	Approved
0.7672	Intermediate Similarity	NPD7503	Approved
0.7521	Intermediate Similarity	NPD8379	Approved
0.7521	Intermediate Similarity	NPD8378	Approved
0.7521	Intermediate Similarity	NPD8296	Approved
0.7521	Intermediate Similarity	NPD8033	Approved
0.7521	Intermediate Similarity	NPD8380	Approved
0.7521	Intermediate Similarity	NPD8335	Approved
0.75	Intermediate Similarity	NPD7524	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7455	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7838	Discovery
0.7436	Intermediate Similarity	NPD8377	Approved
0.7436	Intermediate Similarity	NPD8294	Approved
0.7387	Intermediate Similarity	NPD6686	Approved
0.7212	Intermediate Similarity	NPD7637	Suspended
0.7131	Intermediate Similarity	NPD7507	Approved
0.71	Intermediate Similarity	NPD6695	Phase 3
0.7097	Intermediate Similarity	NPD7319	Approved
0.7091	Intermediate Similarity	NPD7632	Discontinued
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5778	Approved
0.6981	Remote Similarity	NPD5779	Approved
0.6972	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6698	Approved
0.6952	Remote Similarity	NPD46	Approved
0.6923	Remote Similarity	NPD4632	Approved
0.6916	Remote Similarity	NPD7748	Approved
0.686	Remote Similarity	NPD6319	Approved
0.6857	Remote Similarity	NPD6051	Approved
0.6838	Remote Similarity	NPD8297	Approved
0.6832	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7750	Discontinued
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.68	Remote Similarity	NPD6931	Approved
0.68	Remote Similarity	NPD7514	Phase 3
0.68	Remote Similarity	NPD6930	Phase 2
0.68	Remote Similarity	NPD7332	Phase 2
0.6796	Remote Similarity	NPD1694	Approved
0.6783	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD6899	Approved
0.6754	Remote Similarity	NPD7128	Approved
0.6754	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD6675	Approved
0.6754	Remote Similarity	NPD6402	Approved
0.6729	Remote Similarity	NPD7515	Phase 2
0.6729	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD7902	Approved
0.67	Remote Similarity	NPD6929	Approved
0.6696	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD4159	Approved
0.6696	Remote Similarity	NPD5697	Approved
0.6695	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.664	Remote Similarity	NPD7492	Approved
0.6638	Remote Similarity	NPD7320	Approved
0.6633	Remote Similarity	NPD8264	Approved
0.6612	Remote Similarity	NPD6009	Approved
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6847	Approved
0.661	Remote Similarity	NPD6869	Approved
0.661	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6649	Approved
0.6609	Remote Similarity	NPD6008	Approved
0.66	Remote Similarity	NPD7145	Approved
0.6589	Remote Similarity	NPD7260	Phase 2
0.6587	Remote Similarity	NPD6616	Approved
0.6585	Remote Similarity	NPD6054	Approved
0.6581	Remote Similarity	NPD6013	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6581	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6014	Approved
0.6581	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6084	Phase 2
0.6577	Remote Similarity	NPD6083	Phase 2
0.6574	Remote Similarity	NPD7983	Approved
0.6574	Remote Similarity	NPD7087	Discontinued
0.6569	Remote Similarity	NPD6902	Approved
0.6566	Remote Similarity	NPD6933	Approved
0.656	Remote Similarity	NPD7604	Phase 2
0.6555	Remote Similarity	NPD6882	Approved
0.6552	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5701	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6542	Remote Similarity	NPD6101	Approved
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD7078	Approved
0.6535	Remote Similarity	NPD7645	Phase 2
0.6532	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD8133	Approved
0.65	Remote Similarity	NPD6925	Approved
0.65	Remote Similarity	NPD5776	Phase 2
0.6496	Remote Similarity	NPD6011	Approved
0.6484	Remote Similarity	NPD7736	Approved
0.6481	Remote Similarity	NPD3168	Discontinued
0.648	Remote Similarity	NPD6370	Approved
0.6476	Remote Similarity	NPD6893	Approved
0.6475	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7525	Registered
0.6466	Remote Similarity	NPD6640	Phase 3
0.6457	Remote Similarity	NPD6336	Discontinued
0.6455	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7900	Approved
0.6452	Remote Similarity	NPD6059	Approved
0.6429	Remote Similarity	NPD8328	Phase 3
0.6422	Remote Similarity	NPD5284	Approved
0.6422	Remote Similarity	NPD5281	Approved
0.6422	Remote Similarity	NPD6079	Approved
0.6415	Remote Similarity	NPD7521	Approved
0.6415	Remote Similarity	NPD7146	Approved
0.6415	Remote Similarity	NPD5330	Approved
0.6415	Remote Similarity	NPD6684	Approved
0.6415	Remote Similarity	NPD3618	Phase 1
0.6415	Remote Similarity	NPD7334	Approved
0.6415	Remote Similarity	NPD6409	Approved
0.6408	Remote Similarity	NPD6898	Phase 1
0.6406	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD6921	Approved
0.64	Remote Similarity	NPD6015	Approved
0.64	Remote Similarity	NPD6016	Approved
0.6389	Remote Similarity	NPD5328	Approved
0.6387	Remote Similarity	NPD4634	Approved
0.6373	Remote Similarity	NPD6683	Phase 2
0.6372	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD6926	Approved
0.6364	Remote Similarity	NPD6924	Approved
0.6355	Remote Similarity	NPD3573	Approved
0.6355	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5988	Approved
0.6348	Remote Similarity	NPD5211	Phase 2
0.6333	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.63	Remote Similarity	NPD8039	Approved
0.63	Remote Similarity	NPD6942	Approved
0.63	Remote Similarity	NPD7339	Approved
0.6296	Remote Similarity	NPD6672	Approved
0.6296	Remote Similarity	NPD6903	Approved
0.6296	Remote Similarity	NPD5737	Approved
0.6296	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5693	Phase 1
0.6273	Remote Similarity	NPD5694	Approved
0.6273	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7101	Approved
0.624	Remote Similarity	NPD7100	Approved
0.6239	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5141	Approved
0.6238	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4786	Approved
0.6216	Remote Similarity	NPD4202	Approved
0.6214	Remote Similarity	NPD4195	Approved
0.621	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5226	Approved
0.6207	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD5225	Approved
0.6207	Remote Similarity	NPD5224	Approved
0.6195	Remote Similarity	NPD5221	Approved
0.6195	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5222	Approved
0.619	Remote Similarity	NPD5209	Approved
0.619	Remote Similarity	NPD3667	Approved
0.6182	Remote Similarity	NPD5785	Approved
0.6182	Remote Similarity	NPD5692	Phase 3
0.6182	Remote Similarity	NPD5207	Approved
0.6174	Remote Similarity	NPD4700	Approved
0.617	Remote Similarity	NPD7625	Phase 1
0.6168	Remote Similarity	NPD1696	Phase 3
0.6165	Remote Similarity	NPD6845	Suspended
0.6162	Remote Similarity	NPD7150	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