NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	436.12
Volume:	430.755
LogP:	2.982
LogD:	2.558
LogS:	-3.564
# Rotatable Bonds:	4
TPSA:	129.59
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	3.738
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	1.4808391824772116e-05
Pgp-inhibitor:	0.38
Pgp-substrate:	0.394
Human Intestinal Absorption (HIA):	0.327
20% Bioavailability (F20%):	0.422
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	100.29985809326172%
Volume Distribution (VD):	0.357
Pgp-substrate:	1.8444080352783203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.52
CYP2C9-substrate:	0.728
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.403
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	10.026
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.704
Skin Sensitization:	0.914
Carcinogencity:	0.782
Eye Corrosion:	0.003
Eye Irritation:	0.436
Respiratory Toxicity:	0.27

Download Data

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

Natural Product: NPC477300

Natural Product ID:	NPC477300
*Common Name:**	Inoscavin B
IUPAC Name:	(3Z)-6-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3-[(3,4-dihydroxyphenyl)methylidene]-2-methoxy-2-methylfuro[3,2-c]pyran-4-one
Synonyms:
Standard InCHIKey:	RNGFLTFOEGMRRY-PGODXZJGSA-N
Standard InCHI:	InChI=1S/C24H20O8/c1-24(30-2)16(9-14-5-8-18(26)20(28)11-14)22-21(32-24)12-15(31-23(22)29)6-3-13-4-7-17(25)19(27)10-13/h3-12,25-28H,1-2H3/b6-3+,16-9-
SMILES:	CC1(/C(=CC2=CC(=C(C=C2)O)O)/C3=C(O1)C=C(OC3=O)/C=C/C4=CC(=C(C=C4)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480862
PubChem CID:	11590196
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16488146]
NPO33057	Inonotus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	chonan-si, Korea	2005-APR	PMID[16499338]
NPO41437	Inonotus obliquus + Phellinus punctatus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20830471]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	95000	nM	PMID[16499338]

☑ 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 NPC477300 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	360
0.1-0.2	1710
0.2-0.3	4509
0.3-0.4	10371
0.4-0.5	7534
0.5-0.6	4099
0.6-0.7	6159
0.7-0.8	6278
0.8-0.85	1572
0.85-0.9	93
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC311742
0.9531	High Similarity	NPC477301
0.9355	High Similarity	NPC67951
0.935	High Similarity	NPC306100
0.928	High Similarity	NPC118584
0.92	High Similarity	NPC197832
0.9194	High Similarity	NPC285345
0.8846	High Similarity	NPC285361
0.8837	High Similarity	NPC46192
0.8769	High Similarity	NPC208536
0.8769	High Similarity	NPC64111
0.8692	High Similarity	NPC167463
0.8672	High Similarity	NPC288945
0.8613	High Similarity	NPC9218
0.8594	High Similarity	NPC212541
0.8525	High Similarity	NPC131530
0.8519	High Similarity	NPC476870
0.8504	High Similarity	NPC470848
0.8504	High Similarity	NPC470849
0.8492	Intermediate Similarity	NPC241634
0.8492	Intermediate Similarity	NPC141791
0.8492	Intermediate Similarity	NPC263386
0.8467	Intermediate Similarity	NPC220942
0.8421	Intermediate Similarity	NPC217052
0.8421	Intermediate Similarity	NPC329344
0.8421	Intermediate Similarity	NPC237506
0.8421	Intermediate Similarity	NPC32626
0.8413	Intermediate Similarity	NPC275519
0.84	Intermediate Similarity	NPC281277
0.8387	Intermediate Similarity	NPC328593
0.8387	Intermediate Similarity	NPC33749
0.8387	Intermediate Similarity	NPC261453
0.8385	Intermediate Similarity	NPC246704
0.8358	Intermediate Similarity	NPC318799
0.8357	Intermediate Similarity	NPC285550
0.8333	Intermediate Similarity	NPC65791
0.8321	Intermediate Similarity	NPC90431
0.8321	Intermediate Similarity	NPC289459
0.8321	Intermediate Similarity	NPC470572
0.832	Intermediate Similarity	NPC474967
0.832	Intermediate Similarity	NPC233669
0.8309	Intermediate Similarity	NPC34293
0.8309	Intermediate Similarity	NPC106406
0.8309	Intermediate Similarity	NPC287597
0.8309	Intermediate Similarity	NPC886
0.8306	Intermediate Similarity	NPC95381
0.8298	Intermediate Similarity	NPC183824
0.8296	Intermediate Similarity	NPC473285
0.8295	Intermediate Similarity	NPC147654
0.8293	Intermediate Similarity	NPC226250
0.8286	Intermediate Similarity	NPC296643
0.8286	Intermediate Similarity	NPC52664
0.8281	Intermediate Similarity	NPC2058
0.8273	Intermediate Similarity	NPC191280
0.8268	Intermediate Similarity	NPC309434
0.8268	Intermediate Similarity	NPC203124
0.8258	Intermediate Similarity	NPC120225
0.8258	Intermediate Similarity	NPC213552
0.8258	Intermediate Similarity	NPC276014
0.8235	Intermediate Similarity	NPC155209
0.8235	Intermediate Similarity	NPC168799
0.8235	Intermediate Similarity	NPC254398
0.8222	Intermediate Similarity	NPC219677
0.8214	Intermediate Similarity	NPC282291
0.8214	Intermediate Similarity	NPC166137
0.8209	Intermediate Similarity	NPC229784
0.8209	Intermediate Similarity	NPC477294
0.8209	Intermediate Similarity	NPC83062
0.8209	Intermediate Similarity	NPC477293
0.8207	Intermediate Similarity	NPC32197
0.8203	Intermediate Similarity	NPC70084
0.8201	Intermediate Similarity	NPC328273
0.8201	Intermediate Similarity	NPC81515
0.8201	Intermediate Similarity	NPC321184
0.8201	Intermediate Similarity	NPC476383
0.8201	Intermediate Similarity	NPC64141
0.8201	Intermediate Similarity	NPC68092
0.8201	Intermediate Similarity	NPC472350
0.8201	Intermediate Similarity	NPC321638
0.8201	Intermediate Similarity	NPC171134
0.8201	Intermediate Similarity	NPC197316
0.8201	Intermediate Similarity	NPC89105
0.8189	Intermediate Similarity	NPC610
0.8189	Intermediate Similarity	NPC175799
0.8189	Intermediate Similarity	NPC200988
0.8189	Intermediate Similarity	NPC145023
0.8188	Intermediate Similarity	NPC471872
0.8188	Intermediate Similarity	NPC154485
0.8175	Intermediate Similarity	NPC300776
0.8175	Intermediate Similarity	NPC68779
0.8175	Intermediate Similarity	NPC5310
0.8175	Intermediate Similarity	NPC176814
0.8175	Intermediate Similarity	NPC4982
0.8175	Intermediate Similarity	NPC471883
0.8169	Intermediate Similarity	NPC110063
0.8168	Intermediate Similarity	NPC229084
0.8168	Intermediate Similarity	NPC106659
0.8168	Intermediate Similarity	NPC160900
0.8168	Intermediate Similarity	NPC18984
0.8163	Intermediate Similarity	NPC44730
0.8162	Intermediate Similarity	NPC25581
0.8162	Intermediate Similarity	NPC473924
0.8162	Intermediate Similarity	NPC18074
0.8162	Intermediate Similarity	NPC5419
0.8162	Intermediate Similarity	NPC61
0.8156	Intermediate Similarity	NPC140502
0.8156	Intermediate Similarity	NPC157816
0.8154	Intermediate Similarity	NPC472271
0.8143	Intermediate Similarity	NPC475530
0.8143	Intermediate Similarity	NPC473799
0.8138	Intermediate Similarity	NPC478242
0.8134	Intermediate Similarity	NPC110313
0.8134	Intermediate Similarity	NPC232880
0.8129	Intermediate Similarity	NPC78363
0.8129	Intermediate Similarity	NPC279676
0.8129	Intermediate Similarity	NPC67349
0.8129	Intermediate Similarity	NPC260425
0.8125	Intermediate Similarity	NPC86198
0.8125	Intermediate Similarity	NPC311091
0.8125	Intermediate Similarity	NPC471033
0.812	Intermediate Similarity	NPC303680
0.812	Intermediate Similarity	NPC147192
0.812	Intermediate Similarity	NPC84076
0.812	Intermediate Similarity	NPC475695
0.812	Intermediate Similarity	NPC90128
0.8116	Intermediate Similarity	NPC123988
0.8116	Intermediate Similarity	NPC113295
0.8112	Intermediate Similarity	NPC216819
0.8112	Intermediate Similarity	NPC83743
0.8112	Intermediate Similarity	NPC262182
0.8112	Intermediate Similarity	NPC287615
0.8099	Intermediate Similarity	NPC478239
0.8099	Intermediate Similarity	NPC192831
0.8099	Intermediate Similarity	NPC277315
0.8099	Intermediate Similarity	NPC43158
0.8099	Intermediate Similarity	NPC472016
0.8099	Intermediate Similarity	NPC258469
0.8095	Intermediate Similarity	NPC217472
0.8095	Intermediate Similarity	NPC203664
0.8088	Intermediate Similarity	NPC198388
0.8085	Intermediate Similarity	NPC476385
0.8085	Intermediate Similarity	NPC186406
0.8085	Intermediate Similarity	NPC134405
0.8085	Intermediate Similarity	NPC47471
0.8085	Intermediate Similarity	NPC476377
0.8082	Intermediate Similarity	NPC69367
0.808	Intermediate Similarity	NPC51698
0.8077	Intermediate Similarity	NPC471877
0.8077	Intermediate Similarity	NPC224814
0.8077	Intermediate Similarity	NPC14007
0.8077	Intermediate Similarity	NPC189844
0.8077	Intermediate Similarity	NPC158949
0.8077	Intermediate Similarity	NPC60962
0.8077	Intermediate Similarity	NPC109083
0.8077	Intermediate Similarity	NPC204466
0.8077	Intermediate Similarity	NPC269843
0.8074	Intermediate Similarity	NPC94810
0.8074	Intermediate Similarity	NPC241354
0.8071	Intermediate Similarity	NPC205195
0.8071	Intermediate Similarity	NPC226005
0.8069	Intermediate Similarity	NPC1580
0.8062	Intermediate Similarity	NPC470214
0.8062	Intermediate Similarity	NPC109371
0.8062	Intermediate Similarity	NPC470215
0.806	Intermediate Similarity	NPC476873
0.806	Intermediate Similarity	NPC123228
0.806	Intermediate Similarity	NPC5018
0.806	Intermediate Similarity	NPC123722
0.806	Intermediate Similarity	NPC151167
0.806	Intermediate Similarity	NPC276466
0.8058	Intermediate Similarity	NPC157554
0.8058	Intermediate Similarity	NPC120852
0.8045	Intermediate Similarity	NPC132921
0.8045	Intermediate Similarity	NPC280767
0.8043	Intermediate Similarity	NPC135127
0.8043	Intermediate Similarity	NPC248150
0.8042	Intermediate Similarity	NPC141455
0.8042	Intermediate Similarity	NPC470130
0.8042	Intermediate Similarity	NPC296954
0.8042	Intermediate Similarity	NPC300894
0.8042	Intermediate Similarity	NPC196063
0.803	Intermediate Similarity	NPC14141
0.803	Intermediate Similarity	NPC477152
0.8028	Intermediate Similarity	NPC471027
0.8028	Intermediate Similarity	NPC222433
0.8028	Intermediate Similarity	NPC91546
0.8028	Intermediate Similarity	NPC477335
0.8028	Intermediate Similarity	NPC35702
0.8028	Intermediate Similarity	NPC206095
0.8028	Intermediate Similarity	NPC297517
0.8028	Intermediate Similarity	NPC265648
0.8028	Intermediate Similarity	NPC224389
0.8028	Intermediate Similarity	NPC13818
0.8016	Intermediate Similarity	NPC148969
0.8015	Intermediate Similarity	NPC70752
0.8014	Intermediate Similarity	NPC288452
0.8014	Intermediate Similarity	NPC471875
0.8014	Intermediate Similarity	NPC476820
0.8014	Intermediate Similarity	NPC274891
0.8014	Intermediate Similarity	NPC156709

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 NPC477300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	924
0.2-0.3	1719
0.3-0.4	2648
0.4-0.5	1897
0.5-0.6	1086
0.6-0.7	396
0.7-0.8	123
0.8-0.85	24
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8201	Intermediate Similarity	NPD7266	Discontinued
0.8168	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD6190	Approved
0.7655	Intermediate Similarity	NPD8166	Discontinued
0.7634	Intermediate Similarity	NPD5536	Phase 2
0.7589	Intermediate Similarity	NPD230	Phase 1
0.7559	Intermediate Similarity	NPD3022	Approved
0.7559	Intermediate Similarity	NPD3021	Approved
0.7548	Intermediate Similarity	NPD6234	Discontinued
0.7469	Intermediate Similarity	NPD7685	Pre-registration
0.7417	Intermediate Similarity	NPD1653	Approved
0.741	Intermediate Similarity	NPD9494	Approved
0.7338	Intermediate Similarity	NPD37	Approved
0.7329	Intermediate Similarity	NPD3818	Discontinued
0.7308	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD4966	Approved
0.7308	Intermediate Similarity	NPD4965	Approved
0.7308	Intermediate Similarity	NPD228	Approved
0.7308	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7095	Approved
0.729	Intermediate Similarity	NPD2801	Approved
0.726	Intermediate Similarity	NPD2935	Discontinued
0.7259	Intermediate Similarity	NPD1357	Approved
0.7255	Intermediate Similarity	NPD3455	Phase 2
0.7254	Intermediate Similarity	NPD3764	Approved
0.7237	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7228	Approved
0.7212	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6233	Phase 2
0.7186	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3027	Phase 3
0.7178	Intermediate Similarity	NPD7054	Approved
0.7174	Intermediate Similarity	NPD9269	Phase 2
0.7163	Intermediate Similarity	NPD5736	Approved
0.7153	Intermediate Similarity	NPD4060	Phase 1
0.7153	Intermediate Similarity	NPD826	Approved
0.7153	Intermediate Similarity	NPD3847	Discontinued
0.7153	Intermediate Similarity	NPD825	Approved
0.7152	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7134	Intermediate Similarity	NPD3817	Phase 2
0.7134	Intermediate Similarity	NPD7472	Approved
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7132	Intermediate Similarity	NPD5585	Approved
0.7132	Intermediate Similarity	NPD1358	Approved
0.7123	Intermediate Similarity	NPD7097	Phase 1
0.7103	Intermediate Similarity	NPD6355	Discontinued
0.7103	Intermediate Similarity	NPD447	Suspended
0.7103	Intermediate Similarity	NPD1933	Approved
0.7101	Intermediate Similarity	NPD1535	Discovery
0.7091	Intermediate Similarity	NPD6797	Phase 2
0.7071	Intermediate Similarity	NPD3225	Approved
0.707	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5283	Phase 1
0.7067	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD1512	Approved
0.7059	Intermediate Similarity	NPD9545	Approved
0.7054	Intermediate Similarity	NPD3134	Approved
0.705	Intermediate Similarity	NPD1481	Phase 2
0.7048	Intermediate Similarity	NPD7251	Discontinued
0.7039	Intermediate Similarity	NPD4357	Discontinued
0.703	Intermediate Similarity	NPD7074	Phase 3
0.7029	Intermediate Similarity	NPD3496	Discontinued
0.7019	Intermediate Similarity	NPD7199	Phase 2
0.7014	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD1934	Approved
0.6993	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5535	Approved
0.6987	Remote Similarity	NPD7028	Phase 2
0.6986	Remote Similarity	NPD555	Phase 2
0.6981	Remote Similarity	NPD3882	Suspended
0.6978	Remote Similarity	NPD3705	Approved
0.6975	Remote Similarity	NPD6232	Discontinued
0.6972	Remote Similarity	NPD257	Approved
0.6972	Remote Similarity	NPD258	Approved
0.6966	Remote Similarity	NPD4062	Phase 3
0.6966	Remote Similarity	NPD259	Phase 1
0.6966	Remote Similarity	NPD6663	Approved
0.6959	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4626	Approved
0.6954	Remote Similarity	NPD4628	Phase 3
0.695	Remote Similarity	NPD1283	Approved
0.6939	Remote Similarity	NPD6653	Approved
0.6935	Remote Similarity	NPD2933	Approved
0.6935	Remote Similarity	NPD2934	Approved
0.6934	Remote Similarity	NPD1894	Discontinued
0.6933	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1613	Approved
0.6918	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD943	Approved
0.6905	Remote Similarity	NPD7808	Phase 3
0.6899	Remote Similarity	NPD5909	Discontinued
0.6897	Remote Similarity	NPD2313	Discontinued
0.6884	Remote Similarity	NPD9268	Approved
0.6883	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2860	Approved
0.688	Remote Similarity	NPD2859	Approved
0.6879	Remote Similarity	NPD4359	Approved
0.6871	Remote Similarity	NPD4340	Discontinued
0.6855	Remote Similarity	NPD1465	Phase 2
0.6853	Remote Similarity	NPD2798	Approved
0.685	Remote Similarity	NPD3020	Approved
0.6848	Remote Similarity	NPD7473	Discontinued
0.6846	Remote Similarity	NPD2799	Discontinued
0.6835	Remote Similarity	NPD1778	Approved
0.6835	Remote Similarity	NPD3019	Approved
0.6835	Remote Similarity	NPD2932	Approved
0.6832	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7458	Discontinued
0.681	Remote Similarity	NPD8127	Discontinued
0.6809	Remote Similarity	NPD1608	Approved
0.6806	Remote Similarity	NPD9569	Approved
0.6803	Remote Similarity	NPD3620	Phase 2
0.6803	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2979	Phase 3
0.68	Remote Similarity	NPD6032	Approved
0.6791	Remote Similarity	NPD969	Suspended
0.6788	Remote Similarity	NPD9493	Approved
0.6788	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6166	Phase 2
0.6788	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1203	Approved
0.6781	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2067	Discontinued
0.6763	Remote Similarity	NPD5691	Approved
0.6761	Remote Similarity	NPD2983	Phase 2
0.6761	Remote Similarity	NPD2982	Phase 2
0.6755	Remote Similarity	NPD2346	Discontinued
0.675	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7240	Approved
0.6746	Remote Similarity	NPD6559	Discontinued
0.6738	Remote Similarity	NPD1281	Approved
0.6738	Remote Similarity	NPD422	Phase 1
0.6736	Remote Similarity	NPD5647	Approved
0.6733	Remote Similarity	NPD7033	Discontinued
0.6733	Remote Similarity	NPD4308	Phase 3
0.6732	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3750	Approved
0.6731	Remote Similarity	NPD6273	Approved
0.673	Remote Similarity	NPD6386	Approved
0.673	Remote Similarity	NPD6385	Approved
0.6725	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5402	Approved
0.669	Remote Similarity	NPD2981	Phase 2
0.669	Remote Similarity	NPD2861	Phase 2
0.6689	Remote Similarity	NPD2438	Suspended
0.6689	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD1242	Phase 1
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD968	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD4380	Phase 2
0.6646	Remote Similarity	NPD2978	Approved
0.6646	Remote Similarity	NPD8455	Phase 2
0.6646	Remote Similarity	NPD2977	Approved
0.6645	Remote Similarity	NPD7440	Discontinued
0.6645	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD275	Approved
0.6644	Remote Similarity	NPD274	Approved
0.6644	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6832	Phase 2
0.6644	Remote Similarity	NPD2614	Approved
0.6643	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1651	Approved
0.6642	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7075	Discontinued
0.6623	Remote Similarity	NPD7003	Approved
0.6622	Remote Similarity	NPD8032	Phase 2
0.6621	Remote Similarity	NPD6584	Phase 3
0.6618	Remote Similarity	NPD7843	Approved
0.6617	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3226	Approved
0.6604	Remote Similarity	NPD3111	Phase 1
0.6604	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2424	Discontinued
0.6601	Remote Similarity	NPD5958	Discontinued
0.6601	Remote Similarity	NPD4534	Discontinued
0.66	Remote Similarity	NPD2492	Phase 1
0.6599	Remote Similarity	NPD9536	Phase 1
0.6599	Remote Similarity	NPD9537	Phase 1
0.6596	Remote Similarity	NPD17	Approved
0.6594	Remote Similarity	NPD6671	Approved
0.6594	Remote Similarity	NPD7157	Approved
0.6594	Remote Similarity	NPD4198	Discontinued
0.6593	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD9570	Approved
0.6577	Remote Similarity	NPD1558	Phase 1
0.6575	Remote Similarity	NPD3018	Phase 2
0.6573	Remote Similarity	NPD9717	Approved
0.6569	Remote Similarity	NPD1241	Discontinued
0.6568	Remote Similarity	NPD7804	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