NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	237.1
Volume:	234.607
LogP:	1.565
LogD:	1.405
LogS:	-3.195
# Rotatable Bonds:	3
TPSA:	67.79
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	3.15
Fsp3:	0.417
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:	-4.771
MDCK Permeability:	4.8839665396371856e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.163
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	56.14472198486328%
Volume Distribution (VD):	0.712
Pgp-substrate:	45.60026550292969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.664
CYP1A2-substrate:	0.397
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	7.178
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.193
Carcinogencity:	0.45
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC264956

Natural Product ID:	NPC264956
*Common Name:**	(3-Hydroxy-2,2-Dimethyl-3H-1-Benzofuran-7-Yl) N-Methylcarbamate
IUPAC Name:	(3-hydroxy-2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate
Synonyms:
Standard InCHIKey:	RHSUJRQZTQNSLL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H15NO4/c1-12(2)10(14)7-5-4-6-8(9(7)17-12)16-11(15)13-3/h4-6,10,14H,1-3H3,(H,13,15)
SMILES:	CC1(C)C(c2cccc(c2O1)OC(=NC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1867082
PubChem CID:	27975
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31125231]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO522	Oenanthe javanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	15.8	nM	PMID[521347]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	1.0	nM	PMID[521347]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	54482.7	nM	PMID[521347]

☑ 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 NPC264956 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	223
0.1-0.2	1352
0.2-0.3	4626
0.3-0.4	12078
0.4-0.5	6235
0.5-0.6	6142
0.6-0.7	9122
0.7-0.8	2658
0.8-0.85	260
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8507	High Similarity	NPC19694
0.8467	Intermediate Similarity	NPC58585
0.8467	Intermediate Similarity	NPC25821
0.8462	Intermediate Similarity	NPC475529
0.8456	Intermediate Similarity	NPC166168
0.8451	Intermediate Similarity	NPC81638
0.8425	Intermediate Similarity	NPC474560
0.8417	Intermediate Similarity	NPC172818
0.8417	Intermediate Similarity	NPC25695
0.8394	Intermediate Similarity	NPC18842
0.8358	Intermediate Similarity	NPC473960
0.8345	Intermediate Similarity	NPC134968
0.8345	Intermediate Similarity	NPC174191
0.8333	Intermediate Similarity	NPC26394
0.831	Intermediate Similarity	NPC471414
0.8309	Intermediate Similarity	NPC166040
0.8309	Intermediate Similarity	NPC270849
0.8309	Intermediate Similarity	NPC26653
0.8308	Intermediate Similarity	NPC135961
0.8298	Intermediate Similarity	NPC292487
0.8296	Intermediate Similarity	NPC469386
0.8286	Intermediate Similarity	NPC477939
0.8286	Intermediate Similarity	NPC54743
0.8286	Intermediate Similarity	NPC104167
0.8286	Intermediate Similarity	NPC29799
0.8286	Intermediate Similarity	NPC209985
0.8286	Intermediate Similarity	NPC156502
0.8286	Intermediate Similarity	NPC263367
0.8286	Intermediate Similarity	NPC177160
0.8286	Intermediate Similarity	NPC10737
0.8276	Intermediate Similarity	NPC162193
0.8273	Intermediate Similarity	NPC470881
0.8273	Intermediate Similarity	NPC16485
0.8273	Intermediate Similarity	NPC87696
0.8261	Intermediate Similarity	NPC230219
0.8258	Intermediate Similarity	NPC470804
0.8252	Intermediate Similarity	NPC253878
0.8248	Intermediate Similarity	NPC472024
0.8248	Intermediate Similarity	NPC80600
0.8248	Intermediate Similarity	NPC220935
0.8244	Intermediate Similarity	NPC177475
0.8244	Intermediate Similarity	NPC148615
0.8244	Intermediate Similarity	NPC35071
0.8235	Intermediate Similarity	NPC470084
0.8227	Intermediate Similarity	NPC477938
0.8214	Intermediate Similarity	NPC61946
0.8209	Intermediate Similarity	NPC94276
0.8209	Intermediate Similarity	NPC109822
0.8207	Intermediate Similarity	NPC43508
0.8207	Intermediate Similarity	NPC476301
0.8201	Intermediate Similarity	NPC263064
0.8201	Intermediate Similarity	NPC6836
0.8201	Intermediate Similarity	NPC475840
0.8195	Intermediate Similarity	NPC209567
0.8194	Intermediate Similarity	NPC46092
0.8188	Intermediate Similarity	NPC277804
0.8182	Intermediate Similarity	NPC87725
0.8182	Intermediate Similarity	NPC473875
0.8182	Intermediate Similarity	NPC263261
0.8175	Intermediate Similarity	NPC158477
0.8175	Intermediate Similarity	NPC190629
0.8175	Intermediate Similarity	NPC218856
0.8175	Intermediate Similarity	NPC202582
0.8175	Intermediate Similarity	NPC226788
0.8175	Intermediate Similarity	NPC470258
0.8175	Intermediate Similarity	NPC222004
0.8175	Intermediate Similarity	NPC210623
0.8175	Intermediate Similarity	NPC248355
0.8175	Intermediate Similarity	NPC285339
0.8175	Intermediate Similarity	NPC3439
0.8175	Intermediate Similarity	NPC97326
0.8175	Intermediate Similarity	NPC273295
0.8169	Intermediate Similarity	NPC473739
0.8169	Intermediate Similarity	NPC236306
0.8169	Intermediate Similarity	NPC183781
0.8169	Intermediate Similarity	NPC232164
0.8168	Intermediate Similarity	NPC181969
0.8168	Intermediate Similarity	NPC320987
0.8162	Intermediate Similarity	NPC41706
0.8162	Intermediate Similarity	NPC183181
0.8162	Intermediate Similarity	NPC319625
0.8162	Intermediate Similarity	NPC118787
0.8162	Intermediate Similarity	NPC292056
0.8162	Intermediate Similarity	NPC163332
0.8162	Intermediate Similarity	NPC111247
0.8162	Intermediate Similarity	NPC147821
0.8156	Intermediate Similarity	NPC16435
0.8156	Intermediate Similarity	NPC227503
0.8156	Intermediate Similarity	NPC472336
0.8156	Intermediate Similarity	NPC269091
0.8156	Intermediate Similarity	NPC230734
0.8156	Intermediate Similarity	NPC474639
0.8156	Intermediate Similarity	NPC472334
0.8156	Intermediate Similarity	NPC306441
0.8156	Intermediate Similarity	NPC302701
0.8148	Intermediate Similarity	NPC470510
0.8143	Intermediate Similarity	NPC251981
0.8143	Intermediate Similarity	NPC478085
0.8143	Intermediate Similarity	NPC49603
0.8143	Intermediate Similarity	NPC48863
0.8143	Intermediate Similarity	NPC13745
0.8143	Intermediate Similarity	NPC193026
0.8143	Intermediate Similarity	NPC187616
0.8138	Intermediate Similarity	NPC283995
0.8138	Intermediate Similarity	NPC217635
0.8138	Intermediate Similarity	NPC470235
0.8138	Intermediate Similarity	NPC79429
0.8138	Intermediate Similarity	NPC471667
0.8138	Intermediate Similarity	NPC129417
0.8129	Intermediate Similarity	NPC252833
0.8129	Intermediate Similarity	NPC261619
0.8129	Intermediate Similarity	NPC61477
0.8129	Intermediate Similarity	NPC2190
0.8129	Intermediate Similarity	NPC126029
0.8129	Intermediate Similarity	NPC15658
0.8129	Intermediate Similarity	NPC299144
0.8129	Intermediate Similarity	NPC219876
0.8129	Intermediate Similarity	NPC78770
0.8129	Intermediate Similarity	NPC185604
0.8125	Intermediate Similarity	NPC476356
0.8125	Intermediate Similarity	NPC41782
0.812	Intermediate Similarity	NPC476343
0.812	Intermediate Similarity	NPC226712
0.8116	Intermediate Similarity	NPC42300
0.8116	Intermediate Similarity	NPC187998
0.8116	Intermediate Similarity	NPC241522
0.8116	Intermediate Similarity	NPC77040
0.8116	Intermediate Similarity	NPC174495
0.8116	Intermediate Similarity	NPC153739
0.8116	Intermediate Similarity	NPC242807
0.8116	Intermediate Similarity	NPC64201
0.8116	Intermediate Similarity	NPC257582
0.8116	Intermediate Similarity	NPC92164
0.8116	Intermediate Similarity	NPC145305
0.8112	Intermediate Similarity	NPC184797
0.8112	Intermediate Similarity	NPC254759
0.8112	Intermediate Similarity	NPC309124
0.8112	Intermediate Similarity	NPC160283
0.8102	Intermediate Similarity	NPC302378
0.8102	Intermediate Similarity	NPC40377
0.8095	Intermediate Similarity	NPC275284
0.8095	Intermediate Similarity	NPC15956
0.8095	Intermediate Similarity	NPC114505
0.8095	Intermediate Similarity	NPC213074
0.8095	Intermediate Similarity	NPC224674
0.8095	Intermediate Similarity	NPC193473
0.8095	Intermediate Similarity	NPC31325
0.8092	Intermediate Similarity	NPC329980
0.8092	Intermediate Similarity	NPC255675
0.8088	Intermediate Similarity	NPC206882
0.8088	Intermediate Similarity	NPC58607
0.8088	Intermediate Similarity	NPC178284
0.8088	Intermediate Similarity	NPC191037
0.8085	Intermediate Similarity	NPC164787
0.8085	Intermediate Similarity	NPC101624
0.8085	Intermediate Similarity	NPC474206
0.8085	Intermediate Similarity	NPC472337
0.8085	Intermediate Similarity	NPC470356
0.8085	Intermediate Similarity	NPC121812
0.8085	Intermediate Similarity	NPC112246
0.8085	Intermediate Similarity	NPC151224
0.8085	Intermediate Similarity	NPC94750
0.8085	Intermediate Similarity	NPC234333
0.8085	Intermediate Similarity	NPC260898
0.8085	Intermediate Similarity	NPC112939
0.8085	Intermediate Similarity	NPC184938
0.8085	Intermediate Similarity	NPC47398
0.8082	Intermediate Similarity	NPC18979
0.8082	Intermediate Similarity	NPC475096
0.8082	Intermediate Similarity	NPC180953
0.8074	Intermediate Similarity	NPC293701
0.8074	Intermediate Similarity	NPC114901
0.8074	Intermediate Similarity	NPC48990
0.8071	Intermediate Similarity	NPC49074
0.8071	Intermediate Similarity	NPC69513
0.8071	Intermediate Similarity	NPC215833
0.8071	Intermediate Similarity	NPC105554
0.8071	Intermediate Similarity	NPC112237
0.8069	Intermediate Similarity	NPC477616
0.8069	Intermediate Similarity	NPC470950
0.8069	Intermediate Similarity	NPC185307
0.806	Intermediate Similarity	NPC71090
0.8058	Intermediate Similarity	NPC42760
0.8058	Intermediate Similarity	NPC268266
0.8058	Intermediate Similarity	NPC469613
0.8058	Intermediate Similarity	NPC9912
0.8058	Intermediate Similarity	NPC30043
0.8058	Intermediate Similarity	NPC472597
0.8058	Intermediate Similarity	NPC268342
0.8058	Intermediate Similarity	NPC469625
0.8058	Intermediate Similarity	NPC220825
0.8058	Intermediate Similarity	NPC65942
0.8058	Intermediate Similarity	NPC248307
0.8056	Intermediate Similarity	NPC311530
0.8054	Intermediate Similarity	NPC98624
0.8043	Intermediate Similarity	NPC86030
0.8043	Intermediate Similarity	NPC5851
0.8043	Intermediate Similarity	NPC475875
0.8042	Intermediate Similarity	NPC292882
0.8041	Intermediate Similarity	NPC270751

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 NPC264956 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	801
0.2-0.3	1742
0.3-0.4	2650
0.4-0.5	1887
0.5-0.6	1109
0.6-0.7	691
0.7-0.8	102
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
0.8298	Intermediate Similarity	NPD1375	Discontinued
0.8129	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1613	Approved
0.812	Intermediate Similarity	NPD1091	Approved
0.7914	Intermediate Similarity	NPD3027	Phase 3
0.7842	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD290	Approved
0.777	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1357	Approved
0.7721	Intermediate Similarity	NPD776	Approved
0.7721	Intermediate Similarity	NPD3705	Approved
0.7692	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD556	Approved
0.7609	Intermediate Similarity	NPD3685	Discontinued
0.76	Intermediate Similarity	NPD1774	Approved
0.7557	Intermediate Similarity	NPD228	Approved
0.7518	Intermediate Similarity	NPD1712	Approved
0.7516	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD5772	Approved
0.7483	Intermediate Similarity	NPD2161	Phase 2
0.7483	Intermediate Similarity	NPD1048	Approved
0.7467	Intermediate Similarity	NPD2677	Approved
0.7463	Intermediate Similarity	NPD709	Approved
0.7452	Intermediate Similarity	NPD2560	Approved
0.7452	Intermediate Similarity	NPD2563	Approved
0.745	Intermediate Similarity	NPD4237	Approved
0.745	Intermediate Similarity	NPD6674	Discontinued
0.745	Intermediate Similarity	NPD5177	Phase 3
0.745	Intermediate Similarity	NPD4236	Phase 3
0.7431	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD839	Approved
0.7431	Intermediate Similarity	NPD840	Approved
0.7403	Intermediate Similarity	NPD3687	Approved
0.7403	Intermediate Similarity	NPD3686	Approved
0.7402	Intermediate Similarity	NPD291	Approved
0.7386	Intermediate Similarity	NPD7526	Approved
0.7386	Intermediate Similarity	NPD52	Approved
0.7386	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1558	Phase 1
0.7333	Intermediate Similarity	NPD6671	Approved
0.7328	Intermediate Similarity	NPD2684	Approved
0.7324	Intermediate Similarity	NPD558	Phase 2
0.732	Intermediate Similarity	NPD4123	Phase 3
0.7308	Intermediate Similarity	NPD4678	Approved
0.7308	Intermediate Similarity	NPD4675	Approved
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7285	Intermediate Similarity	NPD6331	Phase 2
0.7278	Intermediate Similarity	NPD2977	Approved
0.7278	Intermediate Similarity	NPD2978	Approved
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD2424	Discontinued
0.726	Intermediate Similarity	NPD2238	Phase 2
0.7248	Intermediate Similarity	NPD6032	Approved
0.7241	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7843	Approved
0.7234	Intermediate Similarity	NPD4749	Approved
0.7222	Intermediate Similarity	NPD7199	Phase 2
0.7215	Intermediate Similarity	NPD1934	Approved
0.7215	Intermediate Similarity	NPD37	Approved
0.7214	Intermediate Similarity	NPD1610	Phase 2
0.7212	Intermediate Similarity	NPD3818	Discontinued
0.7211	Intermediate Similarity	NPD447	Suspended
0.7206	Intermediate Similarity	NPD7157	Approved
0.72	Intermediate Similarity	NPD5762	Approved
0.72	Intermediate Similarity	NPD5763	Approved
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.7188	Intermediate Similarity	NPD4966	Approved
0.7188	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD4965	Approved
0.7183	Intermediate Similarity	NPD2922	Phase 1
0.7183	Intermediate Similarity	NPD6696	Suspended
0.7179	Intermediate Similarity	NPD4210	Discontinued
0.7178	Intermediate Similarity	NPD6071	Discontinued
0.7174	Intermediate Similarity	NPD1548	Phase 1
0.7163	Intermediate Similarity	NPD2231	Phase 2
0.7163	Intermediate Similarity	NPD2235	Phase 2
0.7162	Intermediate Similarity	NPD2157	Approved
0.7162	Intermediate Similarity	NPD6653	Approved
0.7161	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7134	Intermediate Similarity	NPD3111	Phase 1
0.7134	Intermediate Similarity	NPD2969	Approved
0.7134	Intermediate Similarity	NPD2970	Approved
0.7133	Intermediate Similarity	NPD1794	Approved
0.7124	Intermediate Similarity	NPD2219	Phase 1
0.7115	Intermediate Similarity	NPD5976	Discontinued
0.7105	Intermediate Similarity	NPD4162	Approved
0.7105	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3060	Approved
0.7103	Intermediate Similarity	NPD4908	Phase 1
0.7103	Intermediate Similarity	NPD600	Approved
0.7103	Intermediate Similarity	NPD596	Approved
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7097	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6842	Approved
0.7093	Intermediate Similarity	NPD6841	Approved
0.7093	Intermediate Similarity	NPD6843	Phase 3
0.7086	Intermediate Similarity	NPD6002	Phase 3
0.7086	Intermediate Similarity	NPD6005	Phase 3
0.7086	Intermediate Similarity	NPD6004	Phase 3
0.7086	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3162	Approved
0.7075	Intermediate Similarity	NPD3163	Approved
0.7073	Intermediate Similarity	NPD3051	Approved
0.7071	Intermediate Similarity	NPD1778	Approved
0.7067	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD8651	Approved
0.7059	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD5283	Phase 1
0.7059	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4625	Phase 3
0.7055	Intermediate Similarity	NPD3179	Approved
0.7055	Intermediate Similarity	NPD3180	Approved
0.7047	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6072	Discontinued
0.7042	Intermediate Similarity	NPD2230	Approved
0.7042	Intermediate Similarity	NPD2233	Approved
0.7042	Intermediate Similarity	NPD2232	Approved
0.7039	Intermediate Similarity	NPD7153	Discontinued
0.7039	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3018	Phase 2
0.7032	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4060	Phase 1
0.7025	Intermediate Similarity	NPD4005	Discontinued
0.7024	Intermediate Similarity	NPD7074	Phase 3
0.7013	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3145	Approved
0.7007	Intermediate Similarity	NPD3144	Approved
0.7007	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2122	Discontinued
0.6993	Remote Similarity	NPD1652	Phase 2
0.6988	Remote Similarity	NPD27	Approved
0.6988	Remote Similarity	NPD2489	Approved
0.6986	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD821	Approved
0.6975	Remote Similarity	NPD3882	Suspended
0.6974	Remote Similarity	NPD7266	Discontinued
0.6972	Remote Similarity	NPD422	Phase 1
0.6968	Remote Similarity	NPD3122	Phase 3
0.6966	Remote Similarity	NPD6584	Phase 3
0.6966	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7054	Approved
0.6959	Remote Similarity	NPD7310	Approved
0.6959	Remote Similarity	NPD7313	Approved
0.6959	Remote Similarity	NPD7312	Approved
0.6959	Remote Similarity	NPD7311	Approved
0.6959	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5588	Approved
0.6954	Remote Similarity	NPD2156	Approved
0.6954	Remote Similarity	NPD2154	Approved
0.6954	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2155	Approved
0.6954	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4663	Approved
0.6923	Remote Similarity	NPD7472	Approved
0.6923	Remote Similarity	NPD4357	Discontinued
0.6919	Remote Similarity	NPD7309	Approved
0.6917	Remote Similarity	NPD968	Approved
0.6913	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3620	Phase 2
0.6913	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7228	Approved
0.6901	Remote Similarity	NPD7549	Discontinued
0.6897	Remote Similarity	NPD1819	Approved
0.6897	Remote Similarity	NPD7906	Approved
0.6897	Remote Similarity	NPD1818	Approved
0.6897	Remote Similarity	NPD1817	Approved
0.6897	Remote Similarity	NPD1820	Approved
0.6894	Remote Similarity	NPD5722	Discontinued
0.6894	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4536	Approved
0.6887	Remote Similarity	NPD4538	Approved
0.6887	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6166	Phase 2
0.6886	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4739	Approved
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2982	Phase 2
0.6875	Remote Similarity	NPD2983	Phase 2
0.6871	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6355	Discontinued
0.6867	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5124	Phase 1
0.6863	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4578	Approved
0.686	Remote Similarity	NPD4577	Approved
0.6852	Remote Similarity	NPD2801	Approved
0.6849	Remote Similarity	NPD3691	Phase 2
0.6849	Remote Similarity	NPD3690	Phase 2
0.6846	Remote Similarity	NPD7477	Discontinued

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