NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	450.13
Volume:	448.051
LogP:	3.193
LogD:	2.806
LogS:	-3.84
# Rotatable Bonds:	5
TPSA:	118.59
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.494
Synthetic Accessibility Score:	3.666
Fsp3:	0.16
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.037
MDCK Permeability:	1.5119578165467829e-05
Pgp-inhibitor:	0.899
Pgp-substrate:	0.23
Human Intestinal Absorption (HIA):	0.47
20% Bioavailability (F20%):	0.524
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	100.58898162841797%
Volume Distribution (VD):	0.353
Pgp-substrate:	2.31498122215271%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.831
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.589
CYP3A4-substrate:	0.552

ADMET: Excretion

Clearance (CL):	7.686
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.715
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.253
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.502
Skin Sensitization:	0.597
Carcinogencity:	0.844
Eye Corrosion:	0.003
Eye Irritation:	0.055
Respiratory Toxicity:	0.404

Download Data

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

Natural Product: NPC477301

Natural Product ID:	NPC477301
*Common Name:**	methylinoscavin B
IUPAC Name:	(3Z)-3-[(3,4-dihydroxyphenyl)methylidene]-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-methoxy-2-methylfuro[3,2-c]pyran-4-one
Synonyms:
Standard InCHIKey:	XCJITIROISCLRT-GAGKHWTPSA-N
Standard InCHI:	InChI=1S/C25H22O8/c1-25(31-3)17(10-15-6-8-18(26)20(28)11-15)23-22(33-25)13-16(32-24(23)29)7-4-14-5-9-19(27)21(12-14)30-2/h4-13,26-28H,1-3H3/b7-4+,17-10-
SMILES:	CC1(/C(=C\C2=CC(=C(C=C2)O)O)/C3=C(O1)C=C(OC3=O)/C=C/C4=CC(=C(C=C4)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11676764
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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]

☑ 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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	38000	nM	PMID[16499338]
NPT2	Others	Unspecified		IC50	=	13100	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 NPC477301 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	361
0.1-0.2	1634
0.2-0.3	4401
0.3-0.4	10056
0.4-0.5	7996
0.5-0.6	3995
0.6-0.7	5878
0.7-0.8	6335
0.8-0.85	1891
0.85-0.9	140
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC477300
0.9104	High Similarity	NPC311742
0.8923	High Similarity	NPC67951
0.8915	High Similarity	NPC306100
0.8855	High Similarity	NPC118584
0.8846	High Similarity	NPC246704
0.8779	High Similarity	NPC289459
0.8779	High Similarity	NPC197832
0.8769	High Similarity	NPC285345
0.8759	High Similarity	NPC90431
0.875	High Similarity	NPC2058
0.8714	High Similarity	NPC52664
0.8712	High Similarity	NPC120225
0.8712	High Similarity	NPC213552
0.8712	High Similarity	NPC276014
0.8657	High Similarity	NPC83062
0.8643	High Similarity	NPC282291
0.8643	High Similarity	NPC166137
0.8626	High Similarity	NPC106659
0.8626	High Similarity	NPC229084
0.8626	High Similarity	NPC160900
0.8626	High Similarity	NPC18984
0.8613	High Similarity	NPC176814
0.8613	High Similarity	NPC68779
0.8613	High Similarity	NPC300776
0.8613	High Similarity	NPC5310
0.8613	High Similarity	NPC4982
0.8592	High Similarity	NPC110063
0.8582	High Similarity	NPC157816
0.8582	High Similarity	NPC140502
0.8582	High Similarity	NPC110313
0.8571	High Similarity	NPC303680
0.8571	High Similarity	NPC84076
0.8571	High Similarity	NPC90128
0.8571	High Similarity	NPC44730
0.8552	High Similarity	NPC478242
0.8551	High Similarity	NPC113295
0.8538	High Similarity	NPC189844
0.8538	High Similarity	NPC109083
0.8538	High Similarity	NPC224814
0.8538	High Similarity	NPC204466
0.8538	High Similarity	NPC471877
0.8538	High Similarity	NPC60962
0.8538	High Similarity	NPC14007
0.8538	High Similarity	NPC158949
0.8538	High Similarity	NPC269843
0.8531	High Similarity	NPC83743
0.8531	High Similarity	NPC216819
0.8531	High Similarity	NPC262182
0.8531	High Similarity	NPC287615
0.8521	High Similarity	NPC478239
0.8519	High Similarity	NPC241354
0.8507	High Similarity	NPC123228
0.8507	High Similarity	NPC276466
0.8507	High Similarity	NPC151167
0.8507	High Similarity	NPC123722
0.8507	High Similarity	NPC5018
0.8503	High Similarity	NPC203664
0.85	High Similarity	NPC226005
0.8496	Intermediate Similarity	NPC280767
0.8489	Intermediate Similarity	NPC157554
0.8489	Intermediate Similarity	NPC120852
0.8483	Intermediate Similarity	NPC1580
0.8478	Intermediate Similarity	NPC135127
0.8473	Intermediate Similarity	NPC70752
0.8462	Intermediate Similarity	NPC202474
0.8456	Intermediate Similarity	NPC285361
0.845	Intermediate Similarity	NPC272471
0.845	Intermediate Similarity	NPC137537
0.845	Intermediate Similarity	NPC164706
0.845	Intermediate Similarity	NPC107588
0.845	Intermediate Similarity	NPC70744
0.8444	Intermediate Similarity	NPC46192
0.8444	Intermediate Similarity	NPC478215
0.844	Intermediate Similarity	NPC288452
0.844	Intermediate Similarity	NPC289690
0.8433	Intermediate Similarity	NPC179777
0.8421	Intermediate Similarity	NPC146886
0.8421	Intermediate Similarity	NPC60517
0.8421	Intermediate Similarity	NPC20443
0.8409	Intermediate Similarity	NPC286573
0.8406	Intermediate Similarity	NPC475468
0.8403	Intermediate Similarity	NPC252292
0.8403	Intermediate Similarity	NPC258671
0.8403	Intermediate Similarity	NPC53884
0.8403	Intermediate Similarity	NPC34927
0.8403	Intermediate Similarity	NPC476382
0.8403	Intermediate Similarity	NPC34587
0.8403	Intermediate Similarity	NPC100998
0.8389	Intermediate Similarity	NPC477299
0.8389	Intermediate Similarity	NPC191046
0.8389	Intermediate Similarity	NPC194095
0.8389	Intermediate Similarity	NPC327032
0.8382	Intermediate Similarity	NPC64111
0.8382	Intermediate Similarity	NPC208536
0.8382	Intermediate Similarity	NPC304622
0.838	Intermediate Similarity	NPC186406
0.838	Intermediate Similarity	NPC326065
0.838	Intermediate Similarity	NPC29599
0.838	Intermediate Similarity	NPC100675
0.838	Intermediate Similarity	NPC9218
0.8369	Intermediate Similarity	NPC100389
0.8369	Intermediate Similarity	NPC284409
0.8358	Intermediate Similarity	NPC257589
0.8358	Intermediate Similarity	NPC53305
0.8356	Intermediate Similarity	NPC201148
0.8356	Intermediate Similarity	NPC300262
0.8356	Intermediate Similarity	NPC3460
0.8356	Intermediate Similarity	NPC80732
0.8356	Intermediate Similarity	NPC192763
0.8356	Intermediate Similarity	NPC210611
0.8356	Intermediate Similarity	NPC215095
0.8356	Intermediate Similarity	NPC199311
0.8356	Intermediate Similarity	NPC261122
0.8356	Intermediate Similarity	NPC28651
0.8346	Intermediate Similarity	NPC212541
0.8345	Intermediate Similarity	NPC199928
0.8345	Intermediate Similarity	NPC476865
0.8344	Intermediate Similarity	NPC226759
0.8333	Intermediate Similarity	NPC194416
0.8333	Intermediate Similarity	NPC46880
0.8333	Intermediate Similarity	NPC232228
0.8333	Intermediate Similarity	NPC304956
0.8333	Intermediate Similarity	NPC177291
0.8322	Intermediate Similarity	NPC61604
0.8322	Intermediate Similarity	NPC245615
0.8322	Intermediate Similarity	NPC299706
0.8322	Intermediate Similarity	NPC67467
0.8322	Intermediate Similarity	NPC115466
0.8321	Intermediate Similarity	NPC275950
0.8311	Intermediate Similarity	NPC32079
0.831	Intermediate Similarity	NPC110699
0.831	Intermediate Similarity	NPC106055
0.831	Intermediate Similarity	NPC202700
0.8309	Intermediate Similarity	NPC226661
0.8309	Intermediate Similarity	NPC167463
0.8308	Intermediate Similarity	NPC277460
0.8299	Intermediate Similarity	NPC90896
0.8299	Intermediate Similarity	NPC283839
0.8299	Intermediate Similarity	NPC111785
0.8298	Intermediate Similarity	NPC281780
0.8298	Intermediate Similarity	NPC126206
0.8296	Intermediate Similarity	NPC127937
0.8296	Intermediate Similarity	NPC92207
0.8296	Intermediate Similarity	NPC274356
0.8288	Intermediate Similarity	NPC283081
0.8288	Intermediate Similarity	NPC143892
0.8288	Intermediate Similarity	NPC232992
0.8288	Intermediate Similarity	NPC299090
0.8288	Intermediate Similarity	NPC221383
0.8286	Intermediate Similarity	NPC476870
0.8284	Intermediate Similarity	NPC288945
0.8278	Intermediate Similarity	NPC471405
0.8276	Intermediate Similarity	NPC476864
0.8276	Intermediate Similarity	NPC476869
0.8276	Intermediate Similarity	NPC476868
0.8276	Intermediate Similarity	NPC476866
0.8261	Intermediate Similarity	NPC476345
0.8255	Intermediate Similarity	NPC476434
0.8255	Intermediate Similarity	NPC36130
0.8255	Intermediate Similarity	NPC134905
0.8244	Intermediate Similarity	NPC57501
0.8244	Intermediate Similarity	NPC69670
0.8243	Intermediate Similarity	NPC188393
0.8243	Intermediate Similarity	NPC470934
0.8239	Intermediate Similarity	NPC220942
0.8231	Intermediate Similarity	NPC280001
0.8231	Intermediate Similarity	NPC472969
0.8231	Intermediate Similarity	NPC478237
0.8227	Intermediate Similarity	NPC471664
0.8227	Intermediate Similarity	NPC471988
0.8227	Intermediate Similarity	NPC37468
0.8227	Intermediate Similarity	NPC471665
0.8227	Intermediate Similarity	NPC186418
0.8224	Intermediate Similarity	NPC475663
0.8224	Intermediate Similarity	NPC133984
0.8224	Intermediate Similarity	NPC286919
0.8224	Intermediate Similarity	NPC472860
0.8219	Intermediate Similarity	NPC98356
0.8214	Intermediate Similarity	NPC67247
0.8214	Intermediate Similarity	NPC111635
0.8214	Intermediate Similarity	NPC473054
0.8214	Intermediate Similarity	NPC471110
0.8212	Intermediate Similarity	NPC10205
0.8212	Intermediate Similarity	NPC38699
0.8212	Intermediate Similarity	NPC131532
0.8209	Intermediate Similarity	NPC242372
0.8209	Intermediate Similarity	NPC164778
0.8209	Intermediate Similarity	NPC257976
0.8209	Intermediate Similarity	NPC4181
0.8207	Intermediate Similarity	NPC292443
0.8207	Intermediate Similarity	NPC476867
0.8207	Intermediate Similarity	NPC160378
0.8207	Intermediate Similarity	NPC297342
0.8201	Intermediate Similarity	NPC111888
0.82	Intermediate Similarity	NPC157898
0.8195	Intermediate Similarity	NPC114845
0.8195	Intermediate Similarity	NPC193484
0.8194	Intermediate Similarity	NPC253722
0.8194	Intermediate Similarity	NPC31751

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 NPC477301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	902
0.2-0.3	1753
0.3-0.4	2618
0.4-0.5	1908
0.5-0.6	1075
0.6-0.7	422
0.7-0.8	117
0.8-0.85	27
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8626	High Similarity	NPD4379	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD5536	Phase 2
0.7986	Intermediate Similarity	NPD7266	Discontinued
0.7935	Intermediate Similarity	NPD6234	Discontinued
0.7842	Intermediate Similarity	NPD9494	Approved
0.784	Intermediate Similarity	NPD7685	Pre-registration
0.7815	Intermediate Similarity	NPD1653	Approved
0.777	Intermediate Similarity	NPD6190	Approved
0.7769	Intermediate Similarity	NPD228	Approved
0.7727	Intermediate Similarity	NPD37	Approved
0.7704	Intermediate Similarity	NPD1357	Approved
0.7702	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7677	Intermediate Similarity	NPD2801	Approved
0.7632	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7095	Approved
0.7606	Intermediate Similarity	NPD3027	Phase 3
0.7593	Intermediate Similarity	NPD7228	Approved
0.758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7054	Approved
0.7545	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5283	Phase 1
0.7517	Intermediate Similarity	NPD1933	Approved
0.7517	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.7467	Intermediate Similarity	NPD4110	Phase 3
0.7467	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1358	Approved
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7434	Intermediate Similarity	NPD4357	Discontinued
0.7432	Intermediate Similarity	NPD2935	Discontinued
0.7431	Intermediate Similarity	NPD6798	Discontinued
0.7415	Intermediate Similarity	NPD7097	Phase 1
0.741	Intermediate Similarity	NPD3705	Approved
0.7397	Intermediate Similarity	NPD6355	Discontinued
0.7397	Intermediate Similarity	NPD230	Phase 1
0.7394	Intermediate Similarity	NPD7074	Phase 3
0.7391	Intermediate Similarity	NPD7199	Phase 2
0.7389	Intermediate Similarity	NPD1934	Approved
0.7372	Intermediate Similarity	NPD7028	Phase 2
0.7358	Intermediate Similarity	NPD3882	Suspended
0.7351	Intermediate Similarity	NPD8166	Discontinued
0.7349	Intermediate Similarity	NPD6797	Phase 2
0.7346	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD3847	Discontinued
0.7324	Intermediate Similarity	NPD2797	Approved
0.732	Intermediate Similarity	NPD1511	Approved
0.7319	Intermediate Similarity	NPD5585	Approved
0.731	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7251	Discontinued
0.7301	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1535	Discovery
0.7262	Intermediate Similarity	NPD7808	Phase 3
0.726	Intermediate Similarity	NPD4062	Phase 3
0.7254	Intermediate Similarity	NPD3225	Approved
0.7252	Intermediate Similarity	NPD3134	Approved
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7234	Intermediate Similarity	NPD1481	Phase 2
0.7233	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1465	Phase 2
0.723	Intermediate Similarity	NPD6653	Approved
0.7226	Intermediate Similarity	NPD1512	Approved
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3021	Approved
0.7218	Intermediate Similarity	NPD3022	Approved
0.7214	Intermediate Similarity	NPD3496	Discontinued
0.7212	Intermediate Similarity	NPD7473	Discontinued
0.7211	Intermediate Similarity	NPD1613	Approved
0.7211	Intermediate Similarity	NPD3620	Phase 2
0.7211	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3455	Phase 2
0.7192	Intermediate Similarity	NPD3268	Approved
0.7185	Intermediate Similarity	NPD5535	Approved
0.7183	Intermediate Similarity	NPD2983	Phase 2
0.7183	Intermediate Similarity	NPD2982	Phase 2
0.7178	Intermediate Similarity	NPD8127	Discontinued
0.7162	Intermediate Similarity	NPD4340	Discontinued
0.7152	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6166	Phase 2
0.7152	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4626	Approved
0.7133	Intermediate Similarity	NPD1283	Approved
0.7125	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1894	Discontinued
0.7113	Intermediate Similarity	NPD2981	Phase 2
0.7107	Intermediate Similarity	NPD6386	Approved
0.7107	Intermediate Similarity	NPD6385	Approved
0.7101	Intermediate Similarity	NPD7240	Approved
0.7099	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.7086	Intermediate Similarity	NPD6032	Approved
0.7076	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3764	Approved
0.7075	Intermediate Similarity	NPD2313	Discontinued
0.7063	Intermediate Similarity	NPD4359	Approved
0.7041	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2798	Approved
0.7034	Intermediate Similarity	NPD5647	Approved
0.7021	Intermediate Similarity	NPD1778	Approved
0.702	Intermediate Similarity	NPD2799	Discontinued
0.7019	Intermediate Similarity	NPD2978	Approved
0.7019	Intermediate Similarity	NPD2977	Approved
0.7	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD2492	Phase 1
0.6993	Remote Similarity	NPD1608	Approved
0.6986	Remote Similarity	NPD3018	Phase 2
0.6981	Remote Similarity	NPD3111	Phase 1
0.6981	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2979	Phase 3
0.698	Remote Similarity	NPD1558	Phase 1
0.6975	Remote Similarity	NPD5402	Approved
0.6974	Remote Similarity	NPD2438	Suspended
0.6966	Remote Similarity	NPD1203	Approved
0.6959	Remote Similarity	NPD3144	Approved
0.6959	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3145	Approved
0.695	Remote Similarity	NPD5691	Approved
0.6948	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4380	Phase 2
0.6934	Remote Similarity	NPD7843	Approved
0.6928	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD422	Phase 1
0.6923	Remote Similarity	NPD5844	Phase 1
0.6914	Remote Similarity	NPD8455	Phase 2
0.6913	Remote Similarity	NPD2674	Phase 3
0.6908	Remote Similarity	NPD4308	Phase 3
0.6908	Remote Similarity	NPD7033	Discontinued
0.6906	Remote Similarity	NPD7157	Approved
0.6903	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3750	Approved
0.6899	Remote Similarity	NPD6273	Approved
0.689	Remote Similarity	NPD7075	Discontinued
0.6889	Remote Similarity	NPD2684	Approved
0.6883	Remote Similarity	NPD5958	Discontinued
0.6883	Remote Similarity	NPD4534	Discontinued
0.6883	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2424	Discontinued
0.6879	Remote Similarity	NPD9545	Approved
0.6875	Remote Similarity	NPD824	Approved
0.6875	Remote Similarity	NPD9296	Approved
0.6875	Remote Similarity	NPD9269	Phase 2
0.6871	Remote Similarity	NPD5736	Approved
0.6871	Remote Similarity	NPD2861	Phase 2
0.6867	Remote Similarity	NPD2821	Approved
0.6867	Remote Similarity	NPD825	Approved
0.6867	Remote Similarity	NPD4140	Approved
0.6867	Remote Similarity	NPD826	Approved
0.6866	Remote Similarity	NPD968	Approved
0.6852	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3267	Approved
0.6849	Remote Similarity	NPD3266	Approved
0.6839	Remote Similarity	NPD6674	Discontinued
0.6835	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1651	Approved
0.6828	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6832	Phase 2
0.6824	Remote Similarity	NPD2614	Approved
0.6821	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1375	Discontinued
0.6815	Remote Similarity	NPD7440	Discontinued
0.6813	Remote Similarity	NPD3686	Approved
0.6813	Remote Similarity	NPD3687	Approved
0.681	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1091	Approved
0.6803	Remote Similarity	NPD6584	Phase 3
0.6802	Remote Similarity	NPD7038	Approved
0.6802	Remote Similarity	NPD7039	Approved
0.68	Remote Similarity	NPD8032	Phase 2
0.6796	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7003	Approved
0.6795	Remote Similarity	NPD6331	Phase 2
0.679	Remote Similarity	NPD6873	Phase 2
0.6786	Remote Similarity	NPD6671	Approved
0.6783	Remote Similarity	NPD17	Approved
0.6779	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2653	Approved
0.6772	Remote Similarity	NPD6799	Approved
0.677	Remote Similarity	NPD3226	Approved
0.6763	Remote Similarity	NPD1241	Discontinued
0.6759	Remote Similarity	NPD9717	Approved
0.6752	Remote Similarity	NPD2354	Approved
0.675	Remote Similarity	NPD5403	Approved
0.6748	Remote Similarity	NPD6801	Discontinued
0.6739	Remote Similarity	NPD969	Suspended
0.6739	Remote Similarity	NPD7680	Approved
0.6731	Remote Similarity	NPD1652	Phase 2
0.6731	Remote Similarity	NPD3060	Approved
0.673	Remote Similarity	NPD4739	Approved
0.6724	Remote Similarity	NPD8313	Approved
0.6724	Remote Similarity	NPD8312	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