NPASS Compound

Structure

NPC151704 OpenBabel07101718192D 25 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -0.8660 -1.5000 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 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 8 1 0 0 0 0 2 5 2 0 0 0 0 2 9 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 10 1 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 6 0 0 0 18 19 1 0 0 0 0 18 23 1 6 0 0 0 19 20 1 0 0 0 0 19 23 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.08
Volume:	325.997
LogP:	2.858
LogD:	2.98
LogS:	-3.998
# Rotatable Bonds:	0
TPSA:	71.45
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	4.391
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.047
MDCK Permeability:	2.2725977032678202e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.203
30% Bioavailability (F30%):	0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.349
Plasma Protein Binding (PPB):	97.64727783203125%
Volume Distribution (VD):	0.578
Pgp-substrate:	1.3453704118728638%

ADMET: Metabolism

CYP1A2-inhibitor:	0.302
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.225
CYP2C19-substrate:	0.24
CYP2C9-inhibitor:	0.777
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.514
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	1.176
Half-life (T1/2):	0.44

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.981
Rat Oral Acute Toxicity:	0.374
Maximum Recommended Daily Dose:	0.408
Skin Sensitization:	0.818
Carcinogencity:	0.588
Eye Corrosion:	0.003
Eye Irritation:	0.799
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC151704

Natural Product ID:	NPC151704
*Common Name:**	HDSAIJZBOBVWLA-GUDVDZBRSA-N
IUPAC Name:	n.a.
Synonyms:	SCH-53823
Standard InCHIKey:	HDSAIJZBOBVWLA-GUDVDZBRSA-N
Standard InCHI:	InChI=1S/C20H14O5/c21-12-7-3-6-11-16(12)17(22)18-19(23-18)20(11)24-13-8-1-4-10-5-2-9-14(25-20)15(10)13/h1-9,17-19,21-22H/t17-,18-,19-/m1/s1
SMILES:	Oc1cccc2c1[C@@H](O)[C@H]1O[C@H]1C12Oc2cccc3c2c(O1)ccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL153990
PubChem CID:	9884095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO33512	berkleasmium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25237727]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27592135]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	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	8
MIC	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3
Organism	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[544088]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[544088]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	2050.0	nM	PMID[544089]
NPT2	Others	Unspecified		IC50	=	24000.0	nM	PMID[544087]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	37.5	ug.mL-1	PMID[544088]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	=	37.5	ug.mL-1	PMID[544088]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	25.0	ug.mL-1	PMID[544088]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	37.5	ug.mL-1	PMID[544088]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[544088]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	=	37.5	ug.mL-1	PMID[544088]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	=	32.3	ug.mL-1	PMID[544088]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[544088]

☑ 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 NPC151704 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	518
0.1-0.2	1850
0.2-0.3	5015
0.3-0.4	11213
0.4-0.5	6689
0.5-0.6	4845
0.6-0.7	8514
0.7-0.8	3626
0.8-0.85	397
0.85-0.9	15
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC271076
0.9568	High Similarity	NPC472155
0.95	High Similarity	NPC472154
0.95	High Similarity	NPC23807
0.95	High Similarity	NPC173630
0.9433	High Similarity	NPC288531
0.9348	High Similarity	NPC472151
0.9281	High Similarity	NPC193920
0.9124	High Similarity	NPC138940
0.8859	High Similarity	NPC20050
0.8859	High Similarity	NPC306267
0.8792	High Similarity	NPC233467
0.8693	High Similarity	NPC183402
0.8667	High Similarity	NPC21902
0.8667	High Similarity	NPC134911
0.8667	High Similarity	NPC226108
0.8667	High Similarity	NPC272552
0.8667	High Similarity	NPC44192
0.8667	High Similarity	NPC469944
0.8667	High Similarity	NPC46283
0.8667	High Similarity	NPC322899
0.8639	High Similarity	NPC102280
0.8639	High Similarity	NPC248053
0.8639	High Similarity	NPC155564
0.8636	High Similarity	NPC1253
0.8636	High Similarity	NPC100936
0.8609	High Similarity	NPC78809
0.8581	High Similarity	NPC472153
0.8571	High Similarity	NPC193749
0.8571	High Similarity	NPC284232
0.8552	High Similarity	NPC178054
0.8543	High Similarity	NPC59692
0.8523	High Similarity	NPC175976
0.8514	High Similarity	NPC190714
0.8514	High Similarity	NPC99515
0.8503	High Similarity	NPC469313
0.8503	High Similarity	NPC76176
0.8503	High Similarity	NPC168579
0.8503	High Similarity	NPC171932
0.8503	High Similarity	NPC28440
0.8503	High Similarity	NPC138227
0.8472	Intermediate Similarity	NPC134260
0.8471	Intermediate Similarity	NPC74371
0.8471	Intermediate Similarity	NPC120677
0.8467	Intermediate Similarity	NPC318373
0.8467	Intermediate Similarity	NPC321657
0.8462	Intermediate Similarity	NPC73148
0.8456	Intermediate Similarity	NPC263940
0.8456	Intermediate Similarity	NPC58190
0.8456	Intermediate Similarity	NPC108811
0.8456	Intermediate Similarity	NPC262911
0.8456	Intermediate Similarity	NPC170103
0.8456	Intermediate Similarity	NPC18185
0.8456	Intermediate Similarity	NPC204770
0.8456	Intermediate Similarity	NPC473480
0.8456	Intermediate Similarity	NPC236202
0.8456	Intermediate Similarity	NPC82917
0.8456	Intermediate Similarity	NPC70409
0.8456	Intermediate Similarity	NPC15538
0.8456	Intermediate Similarity	NPC294558
0.8456	Intermediate Similarity	NPC202742
0.8452	Intermediate Similarity	NPC472156
0.844	Intermediate Similarity	NPC121376
0.8435	Intermediate Similarity	NPC163508
0.8435	Intermediate Similarity	NPC252169
0.8435	Intermediate Similarity	NPC472451
0.8435	Intermediate Similarity	NPC173203
0.8435	Intermediate Similarity	NPC473044
0.8435	Intermediate Similarity	NPC37793
0.8429	Intermediate Similarity	NPC218003
0.8425	Intermediate Similarity	NPC277331
0.8425	Intermediate Similarity	NPC210192
0.8425	Intermediate Similarity	NPC100482
0.8421	Intermediate Similarity	NPC474442
0.8418	Intermediate Similarity	NPC75944
0.8418	Intermediate Similarity	NPC11608
0.8418	Intermediate Similarity	NPC297404
0.8414	Intermediate Similarity	NPC292487
0.8403	Intermediate Similarity	NPC234952
0.84	Intermediate Similarity	NPC329836
0.84	Intermediate Similarity	NPC227516
0.84	Intermediate Similarity	NPC20757
0.84	Intermediate Similarity	NPC280945
0.8392	Intermediate Similarity	NPC130496
0.8392	Intermediate Similarity	NPC188555
0.8389	Intermediate Similarity	NPC125755
0.8389	Intermediate Similarity	NPC96576
0.8389	Intermediate Similarity	NPC215678
0.8389	Intermediate Similarity	NPC274454
0.8387	Intermediate Similarity	NPC4809
0.8387	Intermediate Similarity	NPC147743
0.8387	Intermediate Similarity	NPC73517
0.838	Intermediate Similarity	NPC126029
0.838	Intermediate Similarity	NPC303422
0.838	Intermediate Similarity	NPC219876
0.838	Intermediate Similarity	NPC261619
0.838	Intermediate Similarity	NPC78770
0.838	Intermediate Similarity	NPC26080
0.838	Intermediate Similarity	NPC185604
0.838	Intermediate Similarity	NPC85799
0.838	Intermediate Similarity	NPC15658
0.838	Intermediate Similarity	NPC165686
0.838	Intermediate Similarity	NPC61477
0.8378	Intermediate Similarity	NPC304894
0.8378	Intermediate Similarity	NPC15659
0.8378	Intermediate Similarity	NPC473045
0.8378	Intermediate Similarity	NPC25292
0.8367	Intermediate Similarity	NPC472353
0.8367	Intermediate Similarity	NPC186033
0.8367	Intermediate Similarity	NPC475084
0.8365	Intermediate Similarity	NPC175082
0.8365	Intermediate Similarity	NPC472150
0.8356	Intermediate Similarity	NPC182509
0.8356	Intermediate Similarity	NPC174787
0.8356	Intermediate Similarity	NPC262189
0.8356	Intermediate Similarity	NPC213607
0.8356	Intermediate Similarity	NPC22317
0.8356	Intermediate Similarity	NPC109240
0.8355	Intermediate Similarity	NPC259707
0.8355	Intermediate Similarity	NPC471403
0.8345	Intermediate Similarity	NPC262328
0.8345	Intermediate Similarity	NPC87777
0.8345	Intermediate Similarity	NPC474390
0.8344	Intermediate Similarity	NPC476969
0.8344	Intermediate Similarity	NPC211561
0.8344	Intermediate Similarity	NPC48880
0.8333	Intermediate Similarity	NPC106601
0.8333	Intermediate Similarity	NPC151474
0.8333	Intermediate Similarity	NPC159526
0.8333	Intermediate Similarity	NPC15109
0.8333	Intermediate Similarity	NPC185231
0.8333	Intermediate Similarity	NPC164787
0.8333	Intermediate Similarity	NPC471404
0.8333	Intermediate Similarity	NPC205613
0.8333	Intermediate Similarity	NPC86630
0.8333	Intermediate Similarity	NPC153182
0.8333	Intermediate Similarity	NPC212614
0.8333	Intermediate Similarity	NPC11727
0.8333	Intermediate Similarity	NPC227902
0.8333	Intermediate Similarity	NPC79957
0.8333	Intermediate Similarity	NPC174251
0.8333	Intermediate Similarity	NPC61946
0.8333	Intermediate Similarity	NPC238243
0.8322	Intermediate Similarity	NPC474749
0.8322	Intermediate Similarity	NPC11422
0.8322	Intermediate Similarity	NPC115022
0.8322	Intermediate Similarity	NPC178014
0.8322	Intermediate Similarity	NPC42716
0.8322	Intermediate Similarity	NPC475096
0.8322	Intermediate Similarity	NPC161700
0.8322	Intermediate Similarity	NPC294166
0.8322	Intermediate Similarity	NPC277867
0.8313	Intermediate Similarity	NPC103633
0.8311	Intermediate Similarity	NPC81638
0.831	Intermediate Similarity	NPC268342
0.831	Intermediate Similarity	NPC220825
0.831	Intermediate Similarity	NPC268266
0.831	Intermediate Similarity	NPC42760
0.8299	Intermediate Similarity	NPC471389
0.8299	Intermediate Similarity	NPC469661
0.8298	Intermediate Similarity	NPC97326
0.8289	Intermediate Similarity	NPC260781
0.8289	Intermediate Similarity	NPC469707
0.8289	Intermediate Similarity	NPC225815
0.8289	Intermediate Similarity	NPC218041
0.8289	Intermediate Similarity	NPC145979
0.8289	Intermediate Similarity	NPC185955
0.8289	Intermediate Similarity	NPC469706
0.8289	Intermediate Similarity	NPC214326
0.8289	Intermediate Similarity	NPC9933
0.8289	Intermediate Similarity	NPC477612
0.8289	Intermediate Similarity	NPC182368
0.8288	Intermediate Similarity	NPC55947
0.8288	Intermediate Similarity	NPC22517
0.8288	Intermediate Similarity	NPC471388
0.8288	Intermediate Similarity	NPC32630
0.8278	Intermediate Similarity	NPC281549
0.8278	Intermediate Similarity	NPC166584
0.8278	Intermediate Similarity	NPC301961
0.8276	Intermediate Similarity	NPC203230
0.8276	Intermediate Similarity	NPC269091
0.8276	Intermediate Similarity	NPC302701
0.8276	Intermediate Similarity	NPC16435
0.8276	Intermediate Similarity	NPC40664
0.8276	Intermediate Similarity	NPC475628
0.8276	Intermediate Similarity	NPC92932
0.8276	Intermediate Similarity	NPC306441
0.8276	Intermediate Similarity	NPC138350
0.8276	Intermediate Similarity	NPC165482
0.8276	Intermediate Similarity	NPC3293
0.8276	Intermediate Similarity	NPC197723
0.8276	Intermediate Similarity	NPC242028
0.8273	Intermediate Similarity	NPC207179
0.8273	Intermediate Similarity	NPC278552
0.8273	Intermediate Similarity	NPC167571
0.8267	Intermediate Similarity	NPC226540
0.8267	Intermediate Similarity	NPC162193
0.8261	Intermediate Similarity	NPC137460
0.8255	Intermediate Similarity	NPC473108
0.8255	Intermediate Similarity	NPC50250

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 NPC151704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	422
0.1-0.2	903
0.2-0.3	2030
0.3-0.4	2744
0.4-0.5	1566
0.5-0.6	919
0.6-0.7	505
0.7-0.8	56
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
0.8526	High Similarity	NPD3787	Discontinued
0.838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1613	Approved
0.8313	Intermediate Similarity	NPD3751	Discontinued
0.8099	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD4908	Phase 1
0.8028	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1091	Approved
0.7857	Intermediate Similarity	NPD1610	Phase 2
0.7815	Intermediate Similarity	NPD6674	Discontinued
0.7793	Intermediate Similarity	NPD3027	Phase 3
0.7793	Intermediate Similarity	NPD4625	Phase 3
0.7778	Intermediate Similarity	NPD2861	Phase 2
0.7756	Intermediate Similarity	NPD1653	Approved
0.7736	Intermediate Similarity	NPD8455	Phase 2
0.7698	Intermediate Similarity	NPD1548	Phase 1
0.7605	Intermediate Similarity	NPD5844	Phase 1
0.7582	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7199	Phase 2
0.7545	Intermediate Similarity	NPD7228	Approved
0.7531	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7472	Approved
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7453	Intermediate Similarity	NPD37	Approved
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6234	Discontinued
0.7425	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6166	Phase 2
0.7423	Intermediate Similarity	NPD4965	Approved
0.7423	Intermediate Similarity	NPD4967	Phase 2
0.7423	Intermediate Similarity	NPD4966	Approved
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.74	Intermediate Similarity	NPD4060	Phase 1
0.7384	Intermediate Similarity	NPD8313	Approved
0.7384	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4749	Approved
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7365	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6959	Discontinued
0.7346	Intermediate Similarity	NPD1934	Approved
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7213	Phase 3
0.7278	Intermediate Similarity	NPD7212	Phase 2
0.7267	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD2677	Approved
0.7241	Intermediate Similarity	NPD3705	Approved
0.7235	Intermediate Similarity	NPD3818	Discontinued
0.7233	Intermediate Similarity	NPD7447	Phase 1
0.7215	Intermediate Similarity	NPD5058	Phase 3
0.7197	Intermediate Similarity	NPD3750	Approved
0.7195	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1465	Phase 2
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7240	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD290	Approved
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7115	Intermediate Similarity	NPD5762	Approved
0.7115	Intermediate Similarity	NPD5763	Approved
0.7113	Intermediate Similarity	NPD6671	Approved
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7103	Intermediate Similarity	NPD5126	Approved
0.7103	Intermediate Similarity	NPD5125	Phase 3
0.7097	Intermediate Similarity	NPD5960	Phase 3
0.7091	Intermediate Similarity	NPD2801	Approved
0.7089	Intermediate Similarity	NPD3892	Phase 2
0.7081	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD968	Approved
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1511	Approved
0.7045	Intermediate Similarity	NPD8053	Approved
0.7045	Intermediate Similarity	NPD8054	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4536	Approved
0.7032	Intermediate Similarity	NPD4538	Approved
0.7029	Intermediate Similarity	NPD7549	Discontinued
0.7019	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5735	Approved
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.7007	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD709	Approved
0.6987	Remote Similarity	NPD5588	Approved
0.6986	Remote Similarity	NPD5846	Approved
0.6986	Remote Similarity	NPD6516	Phase 2
0.698	Remote Similarity	NPD8651	Approved
0.6975	Remote Similarity	NPD1512	Approved
0.6964	Remote Similarity	NPD3749	Approved
0.6962	Remote Similarity	NPD1549	Phase 2
0.6954	Remote Similarity	NPD3018	Phase 2
0.6948	Remote Similarity	NPD3620	Phase 2
0.6948	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6099	Approved
0.6943	Remote Similarity	NPD6100	Approved
0.6933	Remote Similarity	NPD5403	Approved
0.6919	Remote Similarity	NPD6778	Approved
0.6919	Remote Similarity	NPD6776	Approved
0.6919	Remote Similarity	NPD6782	Approved
0.6919	Remote Similarity	NPD6777	Approved
0.6919	Remote Similarity	NPD6781	Approved
0.6919	Remote Similarity	NPD6779	Approved
0.6919	Remote Similarity	NPD6780	Approved
0.6919	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5401	Approved
0.6913	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7229	Phase 3
0.6892	Remote Similarity	NPD1611	Approved
0.6887	Remote Similarity	NPD6584	Phase 3
0.6886	Remote Similarity	NPD7819	Suspended
0.6879	Remote Similarity	NPD2154	Approved
0.6879	Remote Similarity	NPD2155	Approved
0.6879	Remote Similarity	NPD3748	Approved
0.6879	Remote Similarity	NPD2156	Approved
0.6879	Remote Similarity	NPD4108	Discontinued
0.6879	Remote Similarity	NPD7473	Discontinued
0.6875	Remote Similarity	NPD7157	Approved
0.6872	Remote Similarity	NPD4663	Approved
0.6871	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3225	Approved
0.6867	Remote Similarity	NPD6696	Suspended
0.6864	Remote Similarity	NPD7075	Discontinued
0.6863	Remote Similarity	NPD7095	Approved
0.6857	Remote Similarity	NPD2684	Approved
0.6855	Remote Similarity	NPD7037	Approved
0.6853	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7041	Phase 2
0.6852	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6823	Phase 2
0.6845	Remote Similarity	NPD3817	Phase 2
0.6839	Remote Similarity	NPD4140	Approved
0.6839	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2238	Phase 2
0.6832	Remote Similarity	NPD6190	Approved
0.6831	Remote Similarity	NPD228	Approved
0.6824	Remote Similarity	NPD3496	Discontinued
0.6823	Remote Similarity	NPD7783	Phase 2
0.6823	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7007	Discovery
0.6809	Remote Similarity	NPD7680	Approved
0.6809	Remote Similarity	NPD7435	Discontinued
0.6806	Remote Similarity	NPD8151	Discontinued
0.6805	Remote Similarity	NPD3882	Suspended
0.6803	Remote Similarity	NPD1357	Approved
0.68	Remote Similarity	NPD2982	Phase 2
0.68	Remote Similarity	NPD2983	Phase 2
0.68	Remote Similarity	NPD8156	Discontinued
0.6798	Remote Similarity	NPD4577	Approved
0.6798	Remote Similarity	NPD4578	Approved
0.6795	Remote Similarity	NPD6355	Discontinued
0.6786	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5494	Approved
0.6783	Remote Similarity	NPD7843	Approved
0.678	Remote Similarity	NPD7685	Pre-registration
0.6774	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7870	Phase 2
0.6772	Remote Similarity	NPD7033	Discontinued
0.6772	Remote Similarity	NPD7871	Phase 2
0.677	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4628	Phase 3
0.677	Remote Similarity	NPD7466	Approved
0.6766	Remote Similarity	NPD7411	Suspended
0.6766	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6653	Approved
0.675	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8251	Approved
0.6743	Remote Similarity	NPD8099	Discontinued
0.6743	Remote Similarity	NPD8252	Approved
0.674	Remote Similarity	NPD7906	Approved
0.6736	Remote Similarity	NPD5283	Phase 1
0.6733	Remote Similarity	NPD2235	Phase 2
0.6733	Remote Similarity	NPD2981	Phase 2
0.6733	Remote Similarity	NPD2231	Phase 2
0.6731	Remote Similarity	NPD1558	Phase 1
0.673	Remote Similarity	NPD1551	Phase 2
0.672	Remote Similarity	NPD7697	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