NPASS Compound

Structure

NPC475813 OpenBabel07101718302D 24 26 0 0 1 0 0 0 0 0999 V2000 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 12 2 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 17 1 0 0 0 0 14 20 2 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.11
Volume:	322.632
LogP:	2.842
LogD:	1.954
LogS:	-3.037
# Rotatable Bonds:	2
TPSA:	108.61
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	4.015
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.198
MDCK Permeability:	1.0093718628922943e-05
Pgp-inhibitor:	0.391
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.281
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	90.62657928466797%
Volume Distribution (VD):	0.726
Pgp-substrate:	16.978418350219727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.378
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.268
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	5.59
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.45
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.058
Skin Sensitization:	0.773
Carcinogencity:	0.428
Eye Corrosion:	0.011
Eye Irritation:	0.648
Respiratory Toxicity:	0.326

Download Data

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

Natural Product: NPC475813

Natural Product ID:	NPC475813
*Common Name:**	Ventiloquinone K
IUPAC Name:	n.a.
Synonyms:	Ventiloquinone K
Standard InCHIKey:	UIBXAMHOHCDVSB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O7/c1-6-5-8-9(7(2)24-6)12(18)10-11(16(8)22-3)14(20)17(23-4)15(21)13(10)19/h6-7,18,21H,5H2,1-4H3
SMILES:	COC1=C(O)C(=O)c2c(C1=O)c(OC)c1c(c2O)C(C)OC(C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516573
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001649] Isochromanequinones

*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
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374975]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	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
IC50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[527219]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[527219]
NPT1307	Cell Line	Calu-1	Homo sapiens	IC50	>	100000.0	nM	PMID[527219]
NPT80	Cell Line	Raji	Homo sapiens	IC50	>	100000.0	nM	PMID[527219]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	100000.0	nM	PMID[527219]
NPT1306	Cell Line	WISH	Homo sapiens	IC50	>	100000.0	nM	PMID[527219]

☑ 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 NPC475813 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	377
0.1-0.2	1649
0.2-0.3	4127
0.3-0.4	9941
0.4-0.5	9365
0.5-0.6	4900
0.6-0.7	6775
0.7-0.8	5254
0.8-0.85	286
0.85-0.9	17
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC474630
0.9091	High Similarity	NPC469885
0.9085	High Similarity	NPC283292
0.8897	High Similarity	NPC477409
0.8714	High Similarity	NPC88864
0.8658	High Similarity	NPC112816
0.8581	High Similarity	NPC28632
0.8581	High Similarity	NPC284495
0.8581	High Similarity	NPC313368
0.8571	High Similarity	NPC143898
0.8535	High Similarity	NPC208120
0.8535	High Similarity	NPC173587
0.8523	High Similarity	NPC300540
0.8521	High Similarity	NPC193169
0.8514	High Similarity	NPC274085
0.8514	High Similarity	NPC89664
0.8497	Intermediate Similarity	NPC312482
0.8481	Intermediate Similarity	NPC314653
0.8481	Intermediate Similarity	NPC21016
0.8481	Intermediate Similarity	NPC146584
0.8481	Intermediate Similarity	NPC316262
0.8442	Intermediate Similarity	NPC326910
0.8425	Intermediate Similarity	NPC477408
0.8421	Intermediate Similarity	NPC470568
0.8421	Intermediate Similarity	NPC294646
0.8417	Intermediate Similarity	NPC472047
0.8411	Intermediate Similarity	NPC470479
0.8389	Intermediate Similarity	NPC469385
0.8389	Intermediate Similarity	NPC471451
0.8377	Intermediate Similarity	NPC135522
0.8375	Intermediate Similarity	NPC232936
0.8366	Intermediate Similarity	NPC230848
0.8366	Intermediate Similarity	NPC72958
0.8366	Intermediate Similarity	NPC470569
0.8366	Intermediate Similarity	NPC232645
0.8345	Intermediate Similarity	NPC472599
0.8344	Intermediate Similarity	NPC8817
0.8333	Intermediate Similarity	NPC67197
0.8333	Intermediate Similarity	NPC474637
0.8333	Intermediate Similarity	NPC75694
0.8333	Intermediate Similarity	NPC201127
0.8323	Intermediate Similarity	NPC473096
0.8323	Intermediate Similarity	NPC473095
0.8323	Intermediate Similarity	NPC213416
0.8312	Intermediate Similarity	NPC87708
0.8312	Intermediate Similarity	NPC154683
0.8312	Intermediate Similarity	NPC40356
0.8312	Intermediate Similarity	NPC474843
0.8311	Intermediate Similarity	NPC124365
0.8302	Intermediate Similarity	NPC475055
0.8302	Intermediate Similarity	NPC197168
0.8301	Intermediate Similarity	NPC227122
0.8301	Intermediate Similarity	NPC147735
0.8301	Intermediate Similarity	NPC202595
0.8291	Intermediate Similarity	NPC65746
0.8291	Intermediate Similarity	NPC117985
0.8289	Intermediate Similarity	NPC470359
0.828	Intermediate Similarity	NPC186113
0.8278	Intermediate Similarity	NPC136878
0.8278	Intermediate Similarity	NPC470357
0.8276	Intermediate Similarity	NPC22222
0.8276	Intermediate Similarity	NPC281513
0.8272	Intermediate Similarity	NPC313717
0.8272	Intermediate Similarity	NPC315306
0.8267	Intermediate Similarity	NPC29932
0.8261	Intermediate Similarity	NPC473094
0.8258	Intermediate Similarity	NPC273248
0.8258	Intermediate Similarity	NPC155686
0.8258	Intermediate Similarity	NPC471695
0.8255	Intermediate Similarity	NPC329493
0.825	Intermediate Similarity	NPC25361
0.825	Intermediate Similarity	NPC472049
0.8247	Intermediate Similarity	NPC132990
0.8247	Intermediate Similarity	NPC175617
0.8247	Intermediate Similarity	NPC46882
0.8235	Intermediate Similarity	NPC4423
0.8235	Intermediate Similarity	NPC80370
0.8235	Intermediate Similarity	NPC77325
0.8224	Intermediate Similarity	NPC56433
0.8224	Intermediate Similarity	NPC71055
0.8224	Intermediate Similarity	NPC312929
0.8224	Intermediate Similarity	NPC118027
0.8224	Intermediate Similarity	NPC137296
0.8224	Intermediate Similarity	NPC126767
0.8224	Intermediate Similarity	NPC289042
0.8224	Intermediate Similarity	NPC245584
0.8224	Intermediate Similarity	NPC190648
0.8221	Intermediate Similarity	NPC473113
0.8219	Intermediate Similarity	NPC156967
0.8217	Intermediate Similarity	NPC44199
0.8217	Intermediate Similarity	NPC246466
0.8205	Intermediate Similarity	NPC3898
0.82	Intermediate Similarity	NPC277369
0.82	Intermediate Similarity	NPC476473
0.82	Intermediate Similarity	NPC215451
0.8194	Intermediate Similarity	NPC309430
0.8194	Intermediate Similarity	NPC175978
0.8194	Intermediate Similarity	NPC471349
0.8194	Intermediate Similarity	NPC470340
0.8194	Intermediate Similarity	NPC253904
0.8194	Intermediate Similarity	NPC321363
0.8194	Intermediate Similarity	NPC281272
0.8194	Intermediate Similarity	NPC471347
0.8194	Intermediate Similarity	NPC161778
0.8188	Intermediate Similarity	NPC469818
0.8188	Intermediate Similarity	NPC257003
0.8187	Intermediate Similarity	NPC476822
0.8187	Intermediate Similarity	NPC29055
0.8182	Intermediate Similarity	NPC255641
0.8182	Intermediate Similarity	NPC216917
0.8182	Intermediate Similarity	NPC290954
0.8176	Intermediate Similarity	NPC474186
0.8176	Intermediate Similarity	NPC29771
0.8176	Intermediate Similarity	NPC299405
0.8176	Intermediate Similarity	NPC269117
0.8176	Intermediate Similarity	NPC306835
0.8176	Intermediate Similarity	NPC476477
0.8176	Intermediate Similarity	NPC472261
0.8176	Intermediate Similarity	NPC1268
0.8176	Intermediate Similarity	NPC111422
0.8176	Intermediate Similarity	NPC471602
0.8176	Intermediate Similarity	NPC256463
0.8176	Intermediate Similarity	NPC216312
0.817	Intermediate Similarity	NPC5537
0.8165	Intermediate Similarity	NPC228654
0.8165	Intermediate Similarity	NPC85121
0.8165	Intermediate Similarity	NPC477410
0.8163	Intermediate Similarity	NPC245058
0.8163	Intermediate Similarity	NPC301341
0.8158	Intermediate Similarity	NPC211565
0.8158	Intermediate Similarity	NPC290133
0.8158	Intermediate Similarity	NPC470570
0.8158	Intermediate Similarity	NPC24136
0.8158	Intermediate Similarity	NPC187282
0.8153	Intermediate Similarity	NPC472050
0.8153	Intermediate Similarity	NPC478027
0.8148	Intermediate Similarity	NPC45760
0.8148	Intermediate Similarity	NPC225419
0.8146	Intermediate Similarity	NPC475201
0.8141	Intermediate Similarity	NPC472799
0.8141	Intermediate Similarity	NPC280530
0.8141	Intermediate Similarity	NPC178964
0.8141	Intermediate Similarity	NPC193200
0.8141	Intermediate Similarity	NPC95842
0.8138	Intermediate Similarity	NPC254603
0.8137	Intermediate Similarity	NPC102372
0.8133	Intermediate Similarity	NPC474300
0.8129	Intermediate Similarity	NPC478148
0.8129	Intermediate Similarity	NPC477672
0.8129	Intermediate Similarity	NPC474417
0.8129	Intermediate Similarity	NPC149526
0.8129	Intermediate Similarity	NPC470675
0.8129	Intermediate Similarity	NPC477673
0.8129	Intermediate Similarity	NPC473131
0.8125	Intermediate Similarity	NPC473961
0.8125	Intermediate Similarity	NPC472402
0.8121	Intermediate Similarity	NPC220496
0.8121	Intermediate Similarity	NPC32749
0.8121	Intermediate Similarity	NPC147542
0.8121	Intermediate Similarity	NPC42262
0.8121	Intermediate Similarity	NPC37992
0.8121	Intermediate Similarity	NPC327916
0.8121	Intermediate Similarity	NPC245975
0.8121	Intermediate Similarity	NPC241349
0.8117	Intermediate Similarity	NPC266499
0.8117	Intermediate Similarity	NPC158338
0.8117	Intermediate Similarity	NPC97028
0.8117	Intermediate Similarity	NPC100985
0.8117	Intermediate Similarity	NPC288036
0.8117	Intermediate Similarity	NPC97029
0.8117	Intermediate Similarity	NPC65589
0.8116	Intermediate Similarity	NPC472046
0.8113	Intermediate Similarity	NPC475886
0.8113	Intermediate Similarity	NPC470810
0.8113	Intermediate Similarity	NPC119224
0.8113	Intermediate Similarity	NPC474287
0.8113	Intermediate Similarity	NPC476506
0.8112	Intermediate Similarity	NPC278928
0.811	Intermediate Similarity	NPC477836
0.811	Intermediate Similarity	NPC91650
0.8108	Intermediate Similarity	NPC173980
0.8105	Intermediate Similarity	NPC469425
0.8105	Intermediate Similarity	NPC34802
0.8105	Intermediate Similarity	NPC259632
0.8101	Intermediate Similarity	NPC196448
0.8101	Intermediate Similarity	NPC263483
0.8101	Intermediate Similarity	NPC282390
0.8101	Intermediate Similarity	NPC217677
0.8101	Intermediate Similarity	NPC165977
0.8101	Intermediate Similarity	NPC283301
0.8101	Intermediate Similarity	NPC281137
0.8095	Intermediate Similarity	NPC232996
0.8092	Intermediate Similarity	NPC34482
0.8092	Intermediate Similarity	NPC478019
0.8089	Intermediate Similarity	NPC166054
0.8089	Intermediate Similarity	NPC175192
0.8089	Intermediate Similarity	NPC68727
0.8089	Intermediate Similarity	NPC477687
0.8089	Intermediate Similarity	NPC477671
0.8089	Intermediate Similarity	NPC55662

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 NPC475813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	1121
0.2-0.3	2047
0.3-0.4	2643
0.4-0.5	1827
0.5-0.6	818
0.6-0.7	269
0.7-0.8	85
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD2532	Approved
0.8333	Intermediate Similarity	NPD2533	Approved
0.8333	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD6959	Discontinued
0.7953	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2800	Approved
0.7857	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6651	Approved
0.7799	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5710	Approved
0.7791	Intermediate Similarity	NPD5711	Approved
0.7771	Intermediate Similarity	NPD3226	Approved
0.7748	Intermediate Similarity	NPD2346	Discontinued
0.7688	Intermediate Similarity	NPD7819	Suspended
0.7683	Intermediate Similarity	NPD6232	Discontinued
0.7654	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD7473	Discontinued
0.761	Intermediate Similarity	NPD4380	Phase 2
0.7582	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2935	Discontinued
0.7542	Intermediate Similarity	NPD6781	Approved
0.7542	Intermediate Similarity	NPD6780	Approved
0.7542	Intermediate Similarity	NPD6776	Approved
0.7542	Intermediate Similarity	NPD6779	Approved
0.7542	Intermediate Similarity	NPD6782	Approved
0.7542	Intermediate Similarity	NPD6778	Approved
0.7542	Intermediate Similarity	NPD6777	Approved
0.7531	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1934	Approved
0.7516	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2801	Approved
0.7468	Intermediate Similarity	NPD1549	Phase 2
0.7456	Intermediate Similarity	NPD5844	Phase 1
0.7455	Intermediate Similarity	NPD5494	Approved
0.7423	Intermediate Similarity	NPD5402	Approved
0.7418	Intermediate Similarity	NPD7696	Phase 3
0.7418	Intermediate Similarity	NPD7698	Approved
0.7418	Intermediate Similarity	NPD7697	Approved
0.7407	Intermediate Similarity	NPD6801	Discontinued
0.7394	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1510	Phase 2
0.7381	Intermediate Similarity	NPD6166	Phase 2
0.7381	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3882	Suspended
0.7377	Intermediate Similarity	NPD7871	Phase 2
0.7377	Intermediate Similarity	NPD7870	Phase 2
0.7368	Intermediate Similarity	NPD1607	Approved
0.736	Intermediate Similarity	NPD6534	Approved
0.736	Intermediate Similarity	NPD6535	Approved
0.7353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD6099	Approved
0.733	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7286	Intermediate Similarity	NPD1398	Phase 1
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7283	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7874	Approved
0.7273	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7701	Phase 2
0.7254	Intermediate Similarity	NPD7340	Approved
0.725	Intermediate Similarity	NPD1512	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.7241	Intermediate Similarity	NPD8312	Approved
0.7239	Intermediate Similarity	NPD7411	Suspended
0.7238	Intermediate Similarity	NPD7700	Phase 2
0.7238	Intermediate Similarity	NPD7699	Phase 2
0.7237	Intermediate Similarity	NPD1240	Approved
0.7233	Intermediate Similarity	NPD7390	Discontinued
0.723	Intermediate Similarity	NPD1470	Approved
0.7226	Intermediate Similarity	NPD2796	Approved
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7985	Registered
0.7212	Intermediate Similarity	NPD3817	Phase 2
0.7168	Intermediate Similarity	NPD6797	Phase 2
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7801	Approved
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7125	Intermediate Similarity	NPD6799	Approved
0.7125	Intermediate Similarity	NPD1511	Approved
0.7111	Intermediate Similarity	NPD6213	Phase 3
0.7111	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6212	Phase 3
0.7105	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD1247	Approved
0.7089	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7808	Phase 3
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1201	Approved
0.707	Intermediate Similarity	NPD1471	Phase 3
0.7066	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3787	Discontinued
0.7044	Intermediate Similarity	NPD3750	Approved
0.7044	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3749	Approved
0.7022	Intermediate Similarity	NPD8434	Phase 2
0.7011	Intermediate Similarity	NPD7074	Phase 3
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD1551	Phase 2
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.6994	Remote Similarity	NPD5403	Approved
0.6994	Remote Similarity	NPD3818	Discontinued
0.6989	Remote Similarity	NPD6823	Phase 2
0.6975	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7768	Phase 2
0.6962	Remote Similarity	NPD2344	Approved
0.6957	Remote Similarity	NPD3300	Phase 2
0.6954	Remote Similarity	NPD7054	Approved
0.6943	Remote Similarity	NPD2799	Discontinued
0.6937	Remote Similarity	NPD4628	Phase 3
0.6933	Remote Similarity	NPD6696	Suspended
0.6928	Remote Similarity	NPD4625	Phase 3
0.6915	Remote Similarity	NPD8320	Phase 1
0.6915	Remote Similarity	NPD8319	Approved
0.6914	Remote Similarity	NPD7472	Approved
0.6904	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD405	Clinical (unspecified phase)
0.689	Remote Similarity	NPD920	Approved
0.6886	Remote Similarity	NPD6844	Discontinued
0.6883	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD4749	Approved
0.6859	Remote Similarity	NPD8151	Discontinued
0.6849	Remote Similarity	NPD7644	Approved
0.6846	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1465	Phase 2
0.6842	Remote Similarity	NPD2798	Approved
0.6835	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8366	Approved
0.68	Remote Similarity	NPD7177	Discontinued
0.679	Remote Similarity	NPD2309	Approved
0.6788	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7783	Phase 2
0.6784	Remote Similarity	NPD919	Approved
0.678	Remote Similarity	NPD5953	Discontinued
0.6774	Remote Similarity	NPD411	Approved
0.6761	Remote Similarity	NPD7286	Phase 2
0.6752	Remote Similarity	NPD447	Suspended
0.675	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5761	Phase 2
0.6746	Remote Similarity	NPD5760	Phase 2
0.6738	Remote Similarity	NPD8285	Discontinued
0.6732	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7033	Discontinued
0.673	Remote Similarity	NPD3748	Approved
0.6728	Remote Similarity	NPD7003	Approved
0.6724	Remote Similarity	NPD3926	Phase 2
0.6711	Remote Similarity	NPD4626	Approved
0.6707	Remote Similarity	NPD7458	Discontinued
0.6704	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD9717	Approved
0.6688	Remote Similarity	NPD4060	Phase 1
0.6688	Remote Similarity	NPD2861	Phase 2
0.6686	Remote Similarity	NPD6234	Discontinued
0.6686	Remote Similarity	NPD37	Approved
0.6686	Remote Similarity	NPD2403	Approved
0.6683	Remote Similarity	NPD8491	Approved
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6005	Phase 3
0.6646	Remote Similarity	NPD5124	Phase 1
0.6646	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6002	Phase 3
0.6646	Remote Similarity	NPD230	Phase 1
0.6646	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6832	Phase 2
0.6644	Remote Similarity	NPD5691	Approved
0.6644	Remote Similarity	NPD1651	Approved
0.6625	Remote Similarity	NPD4308	Phase 3
0.6614	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4363	Phase 3
0.6613	Remote Similarity	NPD4360	Phase 2
0.661	Remote Similarity	NPD7893	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