NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	2.464
LogD:	2.098
LogS:	-3.357
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.836
Synthetic Accessibility Score:	3.885
Fsp3:	0.4
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:	-4.884
MDCK Permeability:	8.651641110191122e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.126
Human Intestinal Absorption (HIA):	0.155
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.176

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	88.68824005126953%
Volume Distribution (VD):	0.846
Pgp-substrate:	8.661114692687988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.187
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.49
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	8.179
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.605
Maximum Recommended Daily Dose:	0.324
Skin Sensitization:	0.406
Carcinogencity:	0.359
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.485

Download Data

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

Natural Product: NPC269117

Natural Product ID:	NPC269117
*Common Name:**	Fusarnaphthoquinone B
IUPAC Name:	(8R,9S)-5,9-dihydroxy-8-methoxy-2,4-dimethyl-8,9-dihydro-7H-benzo[g][1]benzofuran-6-one
Synonyms:
Standard InCHIKey:	XLUXTYMYHOLSII-QMTHXVAHSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-6-4-8-7(2)13(17)11-9(16)5-10(19-3)14(18)12(11)15(8)20-6/h4,10,14,17-18H,5H2,1-3H3/t10-,14-/m1/s1
SMILES:	Cc1cc2c(C)c(c3C(=O)C[C@H]([C@H](c3c2o1)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224857
PubChem CID:	46938753
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO32910	fusarium spp. psu-f135	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815366]

☑ 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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	200000.0	nM	PMID[462920]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	200000.0	nM	PMID[462920]

☑ 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 NPC269117 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	397
0.1-0.2	1610
0.2-0.3	3593
0.3-0.4	8796
0.4-0.5	9837
0.5-0.6	3888
0.6-0.7	5855
0.7-0.8	6268
0.8-0.85	2205
0.85-0.9	247
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC24761
0.8987	High Similarity	NPC180924
0.8957	High Similarity	NPC247973
0.8938	High Similarity	NPC470810
0.8931	High Similarity	NPC246647
0.8931	High Similarity	NPC212967
0.8931	High Similarity	NPC164110
0.8931	High Similarity	NPC96342
0.8931	High Similarity	NPC317900
0.8931	High Similarity	NPC476404
0.8931	High Similarity	NPC294300
0.8931	High Similarity	NPC473282
0.8931	High Similarity	NPC104380
0.8931	High Similarity	NPC217602
0.8896	High Similarity	NPC53640
0.8889	High Similarity	NPC133065
0.8889	High Similarity	NPC197168
0.8882	High Similarity	NPC30655
0.8882	High Similarity	NPC96031
0.8882	High Similarity	NPC74854
0.8882	High Similarity	NPC45124
0.8876	High Similarity	NPC228209
0.8861	High Similarity	NPC290927
0.8841	High Similarity	NPC473094
0.8834	High Similarity	NPC326520
0.8834	High Similarity	NPC37183
0.8834	High Similarity	NPC39306
0.8834	High Similarity	NPC25361
0.882	High Similarity	NPC304839
0.882	High Similarity	NPC220582
0.8805	High Similarity	NPC175192
0.8805	High Similarity	NPC148938
0.8788	High Similarity	NPC473095
0.8788	High Similarity	NPC473096
0.878	High Similarity	NPC277480
0.878	High Similarity	NPC170245
0.8773	High Similarity	NPC270837
0.8765	High Similarity	NPC8927
0.8765	High Similarity	NPC66288
0.875	High Similarity	NPC478223
0.8743	High Similarity	NPC98776
0.8742	High Similarity	NPC84721
0.8742	High Similarity	NPC235333
0.8735	High Similarity	NPC315306
0.8735	High Similarity	NPC313717
0.8734	High Similarity	NPC58668
0.8734	High Similarity	NPC106372
0.8721	High Similarity	NPC240808
0.872	High Similarity	NPC291110
0.872	High Similarity	NPC473286
0.8712	High Similarity	NPC84515
0.8712	High Similarity	NPC294965
0.8712	High Similarity	NPC472402
0.8712	High Similarity	NPC81679
0.8712	High Similarity	NPC312056
0.8712	High Similarity	NPC144843
0.8712	High Similarity	NPC478229
0.8704	High Similarity	NPC47623
0.8698	High Similarity	NPC77179
0.8698	High Similarity	NPC246877
0.8698	High Similarity	NPC23553
0.869	High Similarity	NPC227906
0.8688	High Similarity	NPC297531
0.8688	High Similarity	NPC213936
0.8683	High Similarity	NPC247964
0.8679	High Similarity	NPC207624
0.8679	High Similarity	NPC154683
0.8679	High Similarity	NPC40356
0.8671	High Similarity	NPC202595
0.8659	High Similarity	NPC236132
0.8659	High Similarity	NPC329669
0.8659	High Similarity	NPC473313
0.8659	High Similarity	NPC7483
0.8659	High Similarity	NPC472278
0.8659	High Similarity	NPC475985
0.8654	High Similarity	NPC300540
0.865	High Similarity	NPC188486
0.865	High Similarity	NPC474186
0.865	High Similarity	NPC478222
0.8642	High Similarity	NPC196879
0.8642	High Similarity	NPC16935
0.8642	High Similarity	NPC85121
0.8642	High Similarity	NPC476350
0.8642	High Similarity	NPC476349
0.8642	High Similarity	NPC329091
0.8639	High Similarity	NPC8127
0.8639	High Similarity	NPC475233
0.8639	High Similarity	NPC49667
0.8634	High Similarity	NPC164427
0.8634	High Similarity	NPC45131
0.8631	High Similarity	NPC310794
0.8631	High Similarity	NPC65885
0.8625	High Similarity	NPC303950
0.8625	High Similarity	NPC135522
0.8625	High Similarity	NPC158261
0.8625	High Similarity	NPC183874
0.8625	High Similarity	NPC42458
0.8623	High Similarity	NPC17219
0.8623	High Similarity	NPC28042
0.8618	High Similarity	NPC98395
0.8616	High Similarity	NPC193976
0.8616	High Similarity	NPC23668
0.8616	High Similarity	NPC170169
0.8616	High Similarity	NPC72958
0.8616	High Similarity	NPC474772
0.8616	High Similarity	NPC471613
0.8616	High Similarity	NPC115324
0.8616	High Similarity	NPC474744
0.8616	High Similarity	NPC232645
0.8616	High Similarity	NPC472423
0.8616	High Similarity	NPC470569
0.8614	High Similarity	NPC186392
0.8614	High Similarity	NPC95715
0.8614	High Similarity	NPC117854
0.8614	High Similarity	NPC225419
0.8614	High Similarity	NPC6588
0.8614	High Similarity	NPC50394
0.8614	High Similarity	NPC477154
0.8608	High Similarity	NPC178202
0.8606	High Similarity	NPC26386
0.8606	High Similarity	NPC136641
0.8599	High Similarity	NPC469425
0.8598	High Similarity	NPC473961
0.8598	High Similarity	NPC470694
0.8598	High Similarity	NPC216752
0.8589	High Similarity	NPC313368
0.8589	High Similarity	NPC471976
0.8589	High Similarity	NPC84571
0.8589	High Similarity	NPC472962
0.8589	High Similarity	NPC475886
0.8589	High Similarity	NPC228785
0.8589	High Similarity	NPC284495
0.8589	High Similarity	NPC472961
0.8589	High Similarity	NPC14353
0.8589	High Similarity	NPC119224
0.8589	High Similarity	NPC474287
0.8589	High Similarity	NPC56085
0.8588	High Similarity	NPC221820
0.858	High Similarity	NPC10051
0.858	High Similarity	NPC165977
0.858	High Similarity	NPC287243
0.858	High Similarity	NPC477833
0.858	High Similarity	NPC268360
0.858	High Similarity	NPC299094
0.858	High Similarity	NPC217677
0.858	High Similarity	NPC196448
0.8571	High Similarity	NPC198490
0.8571	High Similarity	NPC307286
0.8571	High Similarity	NPC271385
0.8571	High Similarity	NPC30432
0.8571	High Similarity	NPC5029
0.8571	High Similarity	NPC111536
0.8571	High Similarity	NPC76128
0.8571	High Similarity	NPC158226
0.8563	High Similarity	NPC165979
0.8563	High Similarity	NPC163130
0.8563	High Similarity	NPC49487
0.8563	High Similarity	NPC247136
0.8563	High Similarity	NPC99613
0.8562	High Similarity	NPC142308
0.8562	High Similarity	NPC125300
0.8562	High Similarity	NPC474843
0.8562	High Similarity	NPC5871
0.8562	High Similarity	NPC321363
0.8562	High Similarity	NPC87708
0.8562	High Similarity	NPC253904
0.8554	High Similarity	NPC128293
0.8554	High Similarity	NPC29160
0.8554	High Similarity	NPC191012
0.8554	High Similarity	NPC178851
0.8554	High Similarity	NPC255787
0.8553	High Similarity	NPC472421
0.8553	High Similarity	NPC13282
0.8553	High Similarity	NPC78335
0.8553	High Similarity	NPC147735
0.8553	High Similarity	NPC230713
0.8553	High Similarity	NPC167576
0.8553	High Similarity	NPC119929
0.8553	High Similarity	NPC470568
0.8553	High Similarity	NPC294646
0.8547	High Similarity	NPC246153
0.8547	High Similarity	NPC240508
0.8545	High Similarity	NPC39305
0.8545	High Similarity	NPC263092
0.8545	High Similarity	NPC59295
0.8545	High Similarity	NPC1706
0.8545	High Similarity	NPC18100
0.8545	High Similarity	NPC273959
0.8545	High Similarity	NPC477689
0.8545	High Similarity	NPC1755
0.8545	High Similarity	NPC124038
0.8545	High Similarity	NPC100849
0.8544	High Similarity	NPC5537
0.8538	High Similarity	NPC183843
0.8537	High Similarity	NPC61010
0.8537	High Similarity	NPC474187
0.8537	High Similarity	NPC474351
0.8537	High Similarity	NPC311740
0.8537	High Similarity	NPC40491
0.8537	High Similarity	NPC117985

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 NPC269117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	919
0.2-0.3	1814
0.3-0.4	2632
0.4-0.5	1840
0.5-0.6	1023
0.6-0.7	377
0.7-0.8	169
0.8-0.85	20
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8282	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5494	Approved
0.8235	Intermediate Similarity	NPD5844	Phase 1
0.8204	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8171	Intermediate Similarity	NPD2801	Approved
0.8155	Intermediate Similarity	NPD6232	Discontinued
0.8125	Intermediate Similarity	NPD2533	Approved
0.8125	Intermediate Similarity	NPD2532	Approved
0.8125	Intermediate Similarity	NPD2534	Approved
0.8118	Intermediate Similarity	NPD7473	Discontinued
0.811	Intermediate Similarity	NPD1934	Approved
0.8098	Intermediate Similarity	NPD4380	Phase 2
0.8095	Intermediate Similarity	NPD1247	Approved
0.809	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD3818	Discontinued
0.8037	Intermediate Similarity	NPD3226	Approved
0.8025	Intermediate Similarity	NPD2344	Approved
0.7966	Intermediate Similarity	NPD8434	Phase 2
0.7952	Intermediate Similarity	NPD7819	Suspended
0.7917	Intermediate Similarity	NPD7075	Discontinued
0.7901	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4628	Phase 3
0.7862	Intermediate Similarity	NPD1549	Phase 2
0.7849	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6166	Phase 2
0.7849	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7844	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD2309	Approved
0.7811	Intermediate Similarity	NPD3749	Approved
0.7811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD920	Approved
0.7799	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2346	Discontinued
0.7799	Intermediate Similarity	NPD1471	Phase 3
0.7798	Intermediate Similarity	NPD5402	Approved
0.7797	Intermediate Similarity	NPD8312	Approved
0.7797	Intermediate Similarity	NPD8313	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7785	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6777	Approved
0.7784	Intermediate Similarity	NPD6780	Approved
0.7784	Intermediate Similarity	NPD6782	Approved
0.7784	Intermediate Similarity	NPD6781	Approved
0.7784	Intermediate Similarity	NPD6801	Discontinued
0.7784	Intermediate Similarity	NPD6779	Approved
0.7784	Intermediate Similarity	NPD6776	Approved
0.7784	Intermediate Similarity	NPD6778	Approved
0.7771	Intermediate Similarity	NPD6599	Discontinued
0.7771	Intermediate Similarity	NPD1607	Approved
0.7765	Intermediate Similarity	NPD919	Approved
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7751	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1512	Approved
0.7702	Intermediate Similarity	NPD1243	Approved
0.7702	Intermediate Similarity	NPD2800	Approved
0.7692	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1510	Phase 2
0.767	Intermediate Similarity	NPD7074	Phase 3
0.7667	Intermediate Similarity	NPD8150	Discontinued
0.766	Intermediate Similarity	NPD7435	Discontinued
0.7643	Intermediate Similarity	NPD1240	Approved
0.764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD1465	Phase 2
0.7628	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2796	Approved
0.7622	Intermediate Similarity	NPD6799	Approved
0.7614	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7054	Approved
0.7605	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3817	Phase 2
0.7578	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7472	Approved
0.7566	Intermediate Similarity	NPD7698	Approved
0.7566	Intermediate Similarity	NPD7696	Phase 3
0.7566	Intermediate Similarity	NPD7697	Approved
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5711	Approved
0.7529	Intermediate Similarity	NPD5760	Phase 2
0.7529	Intermediate Similarity	NPD5761	Phase 2
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7529	Intermediate Similarity	NPD5710	Approved
0.7528	Intermediate Similarity	NPD6797	Phase 2
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7515	Intermediate Similarity	NPD7411	Suspended
0.7514	Intermediate Similarity	NPD6535	Approved
0.7514	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD7701	Phase 2
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD8151	Discontinued
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7444	Intermediate Similarity	NPD7808	Phase 3
0.7443	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7768	Phase 2
0.743	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7874	Approved
0.7423	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6823	Phase 2
0.7419	Intermediate Similarity	NPD1470	Approved
0.741	Intermediate Similarity	NPD7390	Discontinued
0.7394	Intermediate Similarity	NPD7699	Phase 2
0.7394	Intermediate Similarity	NPD7700	Phase 2
0.7385	Intermediate Similarity	NPD7801	Approved
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5403	Approved
0.7375	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD37	Approved
0.7366	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6212	Phase 3
0.7366	Intermediate Similarity	NPD6213	Phase 3
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6234	Discontinued
0.7341	Intermediate Similarity	NPD4967	Phase 2
0.7341	Intermediate Similarity	NPD4965	Approved
0.7341	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD3750	Approved
0.7322	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD943	Approved
0.7301	Intermediate Similarity	NPD6100	Approved
0.7301	Intermediate Similarity	NPD6099	Approved
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7283	Intermediate Similarity	NPD2296	Approved
0.7262	Intermediate Similarity	NPD5401	Approved
0.7257	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5953	Discontinued
0.7229	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1203	Approved
0.7195	Intermediate Similarity	NPD5408	Approved
0.7195	Intermediate Similarity	NPD5404	Approved
0.7195	Intermediate Similarity	NPD5406	Approved
0.7195	Intermediate Similarity	NPD5405	Approved
0.7175	Intermediate Similarity	NPD7199	Phase 2
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6280	Approved
0.7168	Intermediate Similarity	NPD6279	Approved
0.7168	Intermediate Similarity	NPD6844	Discontinued
0.7167	Intermediate Similarity	NPD7228	Approved
0.7167	Intermediate Similarity	NPD7177	Discontinued
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD230	Phase 1
0.7135	Intermediate Similarity	NPD6808	Phase 2
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6696	Suspended
0.7127	Intermediate Similarity	NPD7286	Phase 2
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4625	Phase 3
0.7118	Intermediate Similarity	NPD6273	Approved
0.7108	Intermediate Similarity	NPD2424	Discontinued
0.7099	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7099	Intermediate Similarity	NPD1613	Approved
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD1651	Approved
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.7077	Intermediate Similarity	NPD8319	Approved
0.7072	Intermediate Similarity	NPD2163	Approved
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3748	Approved
0.7025	Intermediate Similarity	NPD1283	Approved
0.7024	Intermediate Similarity	NPD7003	Approved
0.7012	Intermediate Similarity	NPD6651	Approved
0.7006	Intermediate Similarity	NPD1608	Approved
0.7006	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2861	Phase 2
0.6995	Remote Similarity	NPD8285	Discontinued
0.6994	Remote Similarity	NPD2651	Approved
0.6994	Remote Similarity	NPD2649	Approved
0.6989	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2438	Suspended
0.6982	Remote Similarity	NPD6190	Approved
0.6977	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7985	Registered
0.6975	Remote Similarity	NPD3764	Approved
0.6975	Remote Similarity	NPD6859	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