NPASS Compound

Structure

NPC271076 OpenBabel07101718332D 26 31 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 -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 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 3.4641 -2.0000 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 -2.0000 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 -2.0000 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 1.7321 -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 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 0.8660 -2.5000 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 9 1 0 0 0 0 4 9 1 0 0 0 0 5 12 2 0 0 0 0 6 13 2 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 21 1 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 6 0 0 0 19 20 1 0 0 0 0 19 24 1 6 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	334.787
LogP:	2.724
LogD:	2.743
LogS:	-4.116
# Rotatable Bonds:	0
TPSA:	91.68
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	4.485
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:	-5.39
MDCK Permeability:	1.3513603335013613e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.301
30% Bioavailability (F30%):	0.635

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	97.71710968017578%
Volume Distribution (VD):	0.516
Pgp-substrate:	1.6021513938903809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.208
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.75
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.611
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	2.192
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.944
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.969
Rat Oral Acute Toxicity:	0.8
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.926
Carcinogencity:	0.56
Eye Corrosion:	0.003
Eye Irritation:	0.739
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC271076

Natural Product ID:	NPC271076
*Common Name:**	YUSPOKSZSCPJJV-GUDVDZBRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YUSPOKSZSCPJJV-GUDVDZBRSA-N
Standard InCHI:	InChI=1S/C20H14O6/c21-10-7-8-11(22)16-15(10)17(23)18-19(24-18)20(16)25-12-5-1-3-9-4-2-6-13(26-20)14(9)12/h1-8,17-19,21-23H/t17-,18-,19-/m1/s1
SMILES:	Oc1ccc(c2c1C1(Oc3cccc4c3c(O1)ccc4)[C@H]1[C@@H]([C@@H]2O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342629
PubChem CID:	10247280
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]

☑ 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
MIC	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	7

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[490275]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[490275]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	200.0	ug.mL-1	PMID[490275]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	=	250.0	ug.mL-1	PMID[490275]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	250.0	ug.mL-1	PMID[490275]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	250.0	ug.mL-1	PMID[490275]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[490275]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	=	200.0	ug.mL-1	PMID[490275]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	=	76.7	ug.mL-1	PMID[490275]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[490275]

☑ 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 NPC271076 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	525
0.1-0.2	1893
0.2-0.3	5110
0.3-0.4	11260
0.4-0.5	6601
0.5-0.6	4927
0.6-0.7	8423
0.7-0.8	3572
0.8-0.85	356
0.85-0.9	18
0.9-0.95	4
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC151704
0.9571	High Similarity	NPC23807
0.95	High Similarity	NPC472155
0.9433	High Similarity	NPC472154
0.9433	High Similarity	NPC173630
0.942	High Similarity	NPC472151
0.9366	High Similarity	NPC288531
0.9214	High Similarity	NPC193920
0.9058	High Similarity	NPC138940
0.88	High Similarity	NPC306267
0.88	High Similarity	NPC20050
0.8758	High Similarity	NPC183402
0.8733	High Similarity	NPC233467
0.8701	High Similarity	NPC1253
0.8701	High Similarity	NPC100936
0.8675	High Similarity	NPC78809
0.8636	High Similarity	NPC193749
0.8609	High Similarity	NPC134911
0.8609	High Similarity	NPC46283
0.8609	High Similarity	NPC322899
0.8609	High Similarity	NPC44192
0.8609	High Similarity	NPC226108
0.8609	High Similarity	NPC21902
0.8609	High Similarity	NPC272552
0.8609	High Similarity	NPC469944
0.8591	High Similarity	NPC175976
0.8581	High Similarity	NPC248053
0.8581	High Similarity	NPC155564
0.8581	High Similarity	NPC102280
0.8526	High Similarity	NPC73148
0.8526	High Similarity	NPC472153
0.8511	High Similarity	NPC284232
0.8503	High Similarity	NPC472451
0.8503	High Similarity	NPC252169
0.8493	Intermediate Similarity	NPC178054
0.8487	Intermediate Similarity	NPC59692
0.8481	Intermediate Similarity	NPC297404
0.8481	Intermediate Similarity	NPC11608
0.8456	Intermediate Similarity	NPC99515
0.8456	Intermediate Similarity	NPC190714
0.8446	Intermediate Similarity	NPC469313
0.8446	Intermediate Similarity	NPC138227
0.8446	Intermediate Similarity	NPC171932
0.8446	Intermediate Similarity	NPC76176
0.8446	Intermediate Similarity	NPC28440
0.8446	Intermediate Similarity	NPC168579
0.8418	Intermediate Similarity	NPC74371
0.8418	Intermediate Similarity	NPC120677
0.8414	Intermediate Similarity	NPC134260
0.8411	Intermediate Similarity	NPC476969
0.8411	Intermediate Similarity	NPC321657
0.8411	Intermediate Similarity	NPC318373
0.84	Intermediate Similarity	NPC294558
0.84	Intermediate Similarity	NPC58190
0.84	Intermediate Similarity	NPC202742
0.84	Intermediate Similarity	NPC262911
0.84	Intermediate Similarity	NPC18185
0.84	Intermediate Similarity	NPC70409
0.84	Intermediate Similarity	NPC236202
0.84	Intermediate Similarity	NPC204770
0.84	Intermediate Similarity	NPC227902
0.84	Intermediate Similarity	NPC108811
0.84	Intermediate Similarity	NPC15538
0.84	Intermediate Similarity	NPC263940
0.84	Intermediate Similarity	NPC170103
0.84	Intermediate Similarity	NPC473480
0.84	Intermediate Similarity	NPC82917
0.8397	Intermediate Similarity	NPC472156
0.8389	Intermediate Similarity	NPC11422
0.8389	Intermediate Similarity	NPC474749
0.8389	Intermediate Similarity	NPC178014
0.8389	Intermediate Similarity	NPC42716
0.838	Intermediate Similarity	NPC121376
0.8378	Intermediate Similarity	NPC173203
0.8378	Intermediate Similarity	NPC37793
0.8378	Intermediate Similarity	NPC163508
0.8378	Intermediate Similarity	NPC473044
0.8375	Intermediate Similarity	NPC103633
0.8369	Intermediate Similarity	NPC97326
0.8369	Intermediate Similarity	NPC218003
0.8367	Intermediate Similarity	NPC210192
0.8367	Intermediate Similarity	NPC100482
0.8367	Intermediate Similarity	NPC277331
0.8367	Intermediate Similarity	NPC471389
0.8366	Intermediate Similarity	NPC474442
0.8365	Intermediate Similarity	NPC75944
0.8356	Intermediate Similarity	NPC471388
0.8356	Intermediate Similarity	NPC292487
0.8345	Intermediate Similarity	NPC234952
0.8345	Intermediate Similarity	NPC475628
0.8344	Intermediate Similarity	NPC301961
0.8344	Intermediate Similarity	NPC280945
0.8344	Intermediate Similarity	NPC166584
0.8344	Intermediate Similarity	NPC227516
0.8344	Intermediate Similarity	NPC20757
0.8344	Intermediate Similarity	NPC281549
0.8344	Intermediate Similarity	NPC329836
0.8333	Intermediate Similarity	NPC130496
0.8333	Intermediate Similarity	NPC96576
0.8333	Intermediate Similarity	NPC73517
0.8333	Intermediate Similarity	NPC162193
0.8333	Intermediate Similarity	NPC215678
0.8333	Intermediate Similarity	NPC147743
0.8333	Intermediate Similarity	NPC226540
0.8333	Intermediate Similarity	NPC125755
0.8333	Intermediate Similarity	NPC188555
0.8333	Intermediate Similarity	NPC274454
0.8333	Intermediate Similarity	NPC4809
0.8323	Intermediate Similarity	NPC137460
0.8322	Intermediate Similarity	NPC303422
0.8322	Intermediate Similarity	NPC165686
0.8322	Intermediate Similarity	NPC85799
0.8322	Intermediate Similarity	NPC15659
0.8322	Intermediate Similarity	NPC15658
0.8322	Intermediate Similarity	NPC26080
0.8322	Intermediate Similarity	NPC473045
0.8322	Intermediate Similarity	NPC304894
0.8322	Intermediate Similarity	NPC126029
0.8322	Intermediate Similarity	NPC25292
0.8322	Intermediate Similarity	NPC185604
0.8322	Intermediate Similarity	NPC219876
0.8322	Intermediate Similarity	NPC261619
0.8322	Intermediate Similarity	NPC78770
0.8322	Intermediate Similarity	NPC61477
0.8322	Intermediate Similarity	NPC50250
0.8313	Intermediate Similarity	NPC175082
0.8313	Intermediate Similarity	NPC472150
0.8311	Intermediate Similarity	NPC472353
0.8311	Intermediate Similarity	NPC475084
0.8311	Intermediate Similarity	NPC186033
0.8301	Intermediate Similarity	NPC471403
0.8301	Intermediate Similarity	NPC259707
0.8299	Intermediate Similarity	NPC22317
0.8299	Intermediate Similarity	NPC61783
0.8299	Intermediate Similarity	NPC213607
0.8299	Intermediate Similarity	NPC262189
0.8299	Intermediate Similarity	NPC174787
0.8299	Intermediate Similarity	NPC182509
0.8299	Intermediate Similarity	NPC109240
0.8299	Intermediate Similarity	NPC20520
0.8298	Intermediate Similarity	NPC40377
0.8291	Intermediate Similarity	NPC48880
0.8289	Intermediate Similarity	NPC211561
0.8288	Intermediate Similarity	NPC176051
0.8288	Intermediate Similarity	NPC474282
0.8288	Intermediate Similarity	NPC102904
0.8288	Intermediate Similarity	NPC103976
0.8288	Intermediate Similarity	NPC262328
0.8288	Intermediate Similarity	NPC326797
0.8288	Intermediate Similarity	NPC107551
0.8288	Intermediate Similarity	NPC474390
0.8288	Intermediate Similarity	NPC87777
0.828	Intermediate Similarity	NPC151474
0.828	Intermediate Similarity	NPC205613
0.828	Intermediate Similarity	NPC106601
0.828	Intermediate Similarity	NPC86630
0.828	Intermediate Similarity	NPC159526
0.828	Intermediate Similarity	NPC471404
0.828	Intermediate Similarity	NPC185231
0.828	Intermediate Similarity	NPC212614
0.8278	Intermediate Similarity	NPC174251
0.8278	Intermediate Similarity	NPC153182
0.8276	Intermediate Similarity	NPC61946
0.8276	Intermediate Similarity	NPC164787
0.8276	Intermediate Similarity	NPC15109
0.8276	Intermediate Similarity	NPC472337
0.8276	Intermediate Similarity	NPC79957
0.8276	Intermediate Similarity	NPC238243
0.8276	Intermediate Similarity	NPC11727
0.8267	Intermediate Similarity	NPC475096
0.8267	Intermediate Similarity	NPC277867
0.8267	Intermediate Similarity	NPC161700
0.8267	Intermediate Similarity	NPC307466
0.8264	Intermediate Similarity	NPC294166
0.8264	Intermediate Similarity	NPC115022
0.8255	Intermediate Similarity	NPC81638
0.8252	Intermediate Similarity	NPC220825
0.8252	Intermediate Similarity	NPC42760
0.8252	Intermediate Similarity	NPC268266
0.8252	Intermediate Similarity	NPC268342
0.8243	Intermediate Similarity	NPC469661
0.8235	Intermediate Similarity	NPC214326
0.8235	Intermediate Similarity	NPC225815
0.8235	Intermediate Similarity	NPC185955
0.8235	Intermediate Similarity	NPC182368
0.8235	Intermediate Similarity	NPC9933
0.8235	Intermediate Similarity	NPC477612
0.8235	Intermediate Similarity	NPC238140
0.8235	Intermediate Similarity	NPC260781
0.8235	Intermediate Similarity	NPC218041
0.8235	Intermediate Similarity	NPC145979
0.8235	Intermediate Similarity	NPC469707
0.8235	Intermediate Similarity	NPC469706
0.8231	Intermediate Similarity	NPC319647
0.8231	Intermediate Similarity	NPC25966
0.8231	Intermediate Similarity	NPC127218
0.8231	Intermediate Similarity	NPC55947
0.8231	Intermediate Similarity	NPC22517
0.8231	Intermediate Similarity	NPC245207
0.8231	Intermediate Similarity	NPC32630

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 NPC271076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	909
0.2-0.3	2043
0.3-0.4	2761
0.4-0.5	1545
0.5-0.6	925
0.6-0.7	477
0.7-0.8	58
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD3787	Discontinued
0.8322	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1613	Approved
0.8261	Intermediate Similarity	NPD3751	Discontinued
0.8042	Intermediate Similarity	NPD4908	Phase 1
0.8042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1091	Approved
0.7847	Intermediate Similarity	NPD2861	Phase 2
0.7821	Intermediate Similarity	NPD1653	Approved
0.7801	Intermediate Similarity	NPD1610	Phase 2
0.7763	Intermediate Similarity	NPD6674	Discontinued
0.774	Intermediate Similarity	NPD4625	Phase 3
0.774	Intermediate Similarity	NPD3027	Phase 3
0.7688	Intermediate Similarity	NPD8455	Phase 2
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7643	Intermediate Similarity	NPD1548	Phase 1
0.7532	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7054	Approved
0.7439	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7074	Phase 3
0.7412	Intermediate Similarity	NPD7472	Approved
0.7407	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6234	Discontinued
0.7384	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
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	NPD4965	Approved
0.7378	Intermediate Similarity	NPD4966	Approved
0.7378	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD6797	Phase 2
0.7351	Intermediate Similarity	NPD4060	Phase 1
0.7341	Intermediate Similarity	NPD8313	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4749	Approved
0.7326	Intermediate Similarity	NPD7251	Discontinued
0.7321	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6959	Discontinued
0.7301	Intermediate Similarity	NPD1934	Approved
0.729	Intermediate Similarity	NPD7266	Discontinued
0.7283	Intermediate Similarity	NPD7808	Phase 3
0.7267	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7213	Phase 3
0.7233	Intermediate Similarity	NPD7212	Phase 2
0.7225	Intermediate Similarity	NPD6559	Discontinued
0.7215	Intermediate Similarity	NPD2677	Approved
0.7212	Intermediate Similarity	NPD5402	Approved
0.7193	Intermediate Similarity	NPD3818	Discontinued
0.7192	Intermediate Similarity	NPD3705	Approved
0.7188	Intermediate Similarity	NPD7447	Phase 1
0.7183	Intermediate Similarity	NPD6671	Approved
0.7171	Intermediate Similarity	NPD6233	Phase 2
0.717	Intermediate Similarity	NPD5058	Phase 3
0.7153	Intermediate Similarity	NPD968	Approved
0.7152	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD290	Approved
0.7097	Intermediate Similarity	NPD7097	Phase 1
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7086	Intermediate Similarity	NPD7549	Discontinued
0.7073	Intermediate Similarity	NPD4380	Phase 2
0.707	Intermediate Similarity	NPD5762	Approved
0.707	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD5125	Phase 3
0.7055	Intermediate Similarity	NPD5126	Approved
0.7051	Intermediate Similarity	NPD5960	Phase 3
0.7044	Intermediate Similarity	NPD3892	Phase 2
0.7019	Intermediate Similarity	NPD1511	Approved
0.7006	Intermediate Similarity	NPD8054	Approved
0.7006	Intermediate Similarity	NPD8053	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4538	Approved
0.6987	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4536	Approved
0.6975	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6778	Approved
0.6973	Remote Similarity	NPD6779	Approved
0.6973	Remote Similarity	NPD6782	Approved
0.6973	Remote Similarity	NPD6776	Approved
0.6973	Remote Similarity	NPD6780	Approved
0.6973	Remote Similarity	NPD6781	Approved
0.6973	Remote Similarity	NPD6777	Approved
0.6968	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5124	Phase 1
0.6968	Remote Similarity	NPD5735	Approved
0.6964	Remote Similarity	NPD7768	Phase 2
0.6962	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1611	Approved
0.6959	Remote Similarity	NPD6232	Discontinued
0.6959	Remote Similarity	NPD422	Phase 1
0.6954	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD709	Approved
0.6943	Remote Similarity	NPD5588	Approved
0.6939	Remote Similarity	NPD5846	Approved
0.6939	Remote Similarity	NPD6516	Phase 2
0.6933	Remote Similarity	NPD6696	Suspended
0.6933	Remote Similarity	NPD1512	Approved
0.6933	Remote Similarity	NPD8651	Approved
0.6923	Remote Similarity	NPD3749	Approved
0.6918	Remote Similarity	NPD1549	Phase 2
0.6908	Remote Similarity	NPD3018	Phase 2
0.6905	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3620	Phase 2
0.6903	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6099	Approved
0.6899	Remote Similarity	NPD6100	Approved
0.6898	Remote Similarity	NPD6823	Phase 2
0.6892	Remote Similarity	NPD3496	Discontinued
0.689	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7783	Phase 2
0.6872	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7435	Discontinued
0.686	Remote Similarity	NPD7229	Phase 3
0.6845	Remote Similarity	NPD7819	Suspended
0.6842	Remote Similarity	NPD5494	Approved
0.6842	Remote Similarity	NPD6584	Phase 3
0.6839	Remote Similarity	NPD7473	Discontinued
0.6835	Remote Similarity	NPD2154	Approved
0.6835	Remote Similarity	NPD3748	Approved
0.6835	Remote Similarity	NPD2156	Approved
0.6835	Remote Similarity	NPD4108	Discontinued
0.6835	Remote Similarity	NPD2155	Approved
0.6833	Remote Similarity	NPD4663	Approved
0.6829	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7157	Approved
0.6825	Remote Similarity	NPD7871	Phase 2
0.6825	Remote Similarity	NPD7870	Phase 2
0.6824	Remote Similarity	NPD7075	Discontinued
0.6821	Remote Similarity	NPD3225	Approved
0.6818	Remote Similarity	NPD7095	Approved
0.6813	Remote Similarity	NPD7037	Approved
0.681	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7041	Phase 2
0.6809	Remote Similarity	NPD2684	Approved
0.6806	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3817	Phase 2
0.6795	Remote Similarity	NPD2238	Phase 2
0.6795	Remote Similarity	NPD4140	Approved
0.6795	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6190	Approved
0.6783	Remote Similarity	NPD228	Approved
0.678	Remote Similarity	NPD7007	Discovery
0.6772	Remote Similarity	NPD7698	Approved
0.6772	Remote Similarity	NPD7680	Approved
0.6772	Remote Similarity	NPD7696	Phase 3
0.6772	Remote Similarity	NPD7697	Approved
0.6771	Remote Similarity	NPD8151	Discontinued
0.6765	Remote Similarity	NPD3882	Suspended
0.6761	Remote Similarity	NPD8156	Discontinued
0.676	Remote Similarity	NPD4578	Approved
0.676	Remote Similarity	NPD4577	Approved
0.6757	Remote Similarity	NPD1357	Approved
0.6755	Remote Similarity	NPD2982	Phase 2
0.6755	Remote Similarity	NPD2983	Phase 2
0.6752	Remote Similarity	NPD6355	Discontinued
0.6746	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5929	Approved
0.6742	Remote Similarity	NPD7685	Pre-registration
0.6738	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7843	Approved
0.673	Remote Similarity	NPD7033	Discontinued
0.6728	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7466	Approved
0.6728	Remote Similarity	NPD4628	Phase 3
0.6726	Remote Similarity	NPD7411	Suspended
0.6726	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7701	Phase 2
0.6709	Remote Similarity	NPD6653	Approved
0.6708	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8251	Approved
0.6705	Remote Similarity	NPD8099	Discontinued
0.6705	Remote Similarity	NPD8252	Approved
0.6703	Remote Similarity	NPD7906	Approved
0.6703	Remote Similarity	NPD6534	Approved
0.6703	Remote Similarity	NPD6535	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