NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.14
Volume:	260.839
LogP:	2.116
LogD:	1.713
LogS:	-3.821
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	3.876
Fsp3:	0.714
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:	-4.754
MDCK Permeability:	3.166968235746026e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.546
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	72.40570831298828%
Volume Distribution (VD):	0.697
Pgp-substrate:	33.598934173583984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.573
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.258
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	8.712
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.218
AMES Toxicity:	0.847
Rat Oral Acute Toxicity:	0.765
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.959
Carcinogencity:	0.817
Eye Corrosion:	0.016
Eye Irritation:	0.145
Respiratory Toxicity:	0.703

Download Data

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

Natural Product: NPC473981

Natural Product ID:	NPC473981
*Common Name:**	(3Ar,7Ar)-6-Oxo-2,3,3A,6,7,7A-Hexahydrobenzofuran-3A-Yl Hexanoate
IUPAC Name:	[(3aR,7aR)-6-oxo-2,3,7,7a-tetrahydro-1-benzofuran-3a-yl] hexanoate
Synonyms:
Standard InCHIKey:	IAHVKYZPDVSMEF-OCCSQVGLSA-N
Standard InCHI:	InChI=1S/C14H20O4/c1-2-3-4-5-13(16)18-14-7-6-11(15)10-12(14)17-9-8-14/h6-7,12H,2-5,8-10H2,1H3/t12-,14+/m1/s1
SMILES:	CCCCCC(=O)OC12CCOC1CC(=O)C=C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457081
PubChem CID:	44567069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO33459	cornus controversa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236014]

☑ 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
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.3	ug.mL-1	PMID[553376]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.8	ug.mL-1	PMID[553376]

☑ 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 NPC473981 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	187
0.1-0.2	1378
0.2-0.3	6220
0.3-0.4	14687
0.4-0.5	11637
0.5-0.6	5865
0.6-0.7	2279
0.7-0.8	429
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473980
0.9863	High Similarity	NPC475699
0.9605	High Similarity	NPC475690
0.8333	Intermediate Similarity	NPC474197
0.825	Intermediate Similarity	NPC475210
0.8077	Intermediate Similarity	NPC476355
0.8072	Intermediate Similarity	NPC475947
0.8049	Intermediate Similarity	NPC275507
0.8025	Intermediate Similarity	NPC270126
0.8	Intermediate Similarity	NPC474278
0.8	Intermediate Similarity	NPC41780
0.8	Intermediate Similarity	NPC187568
0.7952	Intermediate Similarity	NPC474252
0.7907	Intermediate Similarity	NPC266957
0.7907	Intermediate Similarity	NPC72513
0.7882	Intermediate Similarity	NPC155873
0.7875	Intermediate Similarity	NPC123360
0.7865	Intermediate Similarity	NPC165383
0.7848	Intermediate Similarity	NPC140287
0.7821	Intermediate Similarity	NPC163003
0.7805	Intermediate Similarity	NPC178277
0.7778	Intermediate Similarity	NPC476028
0.7778	Intermediate Similarity	NPC141789
0.7778	Intermediate Similarity	NPC97516
0.7778	Intermediate Similarity	NPC171204
0.7765	Intermediate Similarity	NPC163615
0.7765	Intermediate Similarity	NPC38569
0.7753	Intermediate Similarity	NPC261607
0.7753	Intermediate Similarity	NPC300312
0.7753	Intermediate Similarity	NPC111114
0.7727	Intermediate Similarity	NPC78008
0.7722	Intermediate Similarity	NPC295633
0.7722	Intermediate Similarity	NPC269206
0.7722	Intermediate Similarity	NPC58956
0.7717	Intermediate Similarity	NPC266842
0.7711	Intermediate Similarity	NPC281132
0.7711	Intermediate Similarity	NPC223904
0.7683	Intermediate Similarity	NPC267231
0.7683	Intermediate Similarity	NPC108816
0.7683	Intermediate Similarity	NPC93763
0.7674	Intermediate Similarity	NPC470755
0.7667	Intermediate Similarity	NPC469692
0.7667	Intermediate Similarity	NPC469645
0.7662	Intermediate Similarity	NPC470256
0.7647	Intermediate Similarity	NPC318468
0.7647	Intermediate Similarity	NPC170286
0.7625	Intermediate Similarity	NPC474280
0.7619	Intermediate Similarity	NPC141810
0.7619	Intermediate Similarity	NPC297440
0.7619	Intermediate Similarity	NPC471325
0.7619	Intermediate Similarity	NPC281949
0.7619	Intermediate Similarity	NPC25684
0.7619	Intermediate Similarity	NPC301477
0.7614	Intermediate Similarity	NPC153570
0.759	Intermediate Similarity	NPC472965
0.759	Intermediate Similarity	NPC63649
0.759	Intermediate Similarity	NPC264227
0.7586	Intermediate Similarity	NPC38576
0.7586	Intermediate Similarity	NPC279859
0.7586	Intermediate Similarity	NPC469483
0.7586	Intermediate Similarity	NPC478112
0.7586	Intermediate Similarity	NPC469910
0.7582	Intermediate Similarity	NPC167219
0.7582	Intermediate Similarity	NPC121825
0.7564	Intermediate Similarity	NPC476591
0.7564	Intermediate Similarity	NPC88877
0.7561	Intermediate Similarity	NPC65603
0.7561	Intermediate Similarity	NPC57744
0.7558	Intermediate Similarity	NPC158756
0.7532	Intermediate Similarity	NPC194871
0.7531	Intermediate Similarity	NPC138408
0.7531	Intermediate Similarity	NPC155587
0.7531	Intermediate Similarity	NPC193351
0.7531	Intermediate Similarity	NPC226669
0.7529	Intermediate Similarity	NPC173609
0.7529	Intermediate Similarity	NPC85772
0.75	Intermediate Similarity	NPC287878
0.75	Intermediate Similarity	NPC469920
0.75	Intermediate Similarity	NPC472007
0.75	Intermediate Similarity	NPC473248
0.7474	Intermediate Similarity	NPC474742
0.7471	Intermediate Similarity	NPC215364
0.7471	Intermediate Similarity	NPC125290
0.7471	Intermediate Similarity	NPC21471
0.7471	Intermediate Similarity	NPC473353
0.7471	Intermediate Similarity	NPC177932
0.7471	Intermediate Similarity	NPC33570
0.747	Intermediate Similarity	NPC128276
0.7444	Intermediate Similarity	NPC144133
0.7444	Intermediate Similarity	NPC49342
0.7444	Intermediate Similarity	NPC251385
0.7444	Intermediate Similarity	NPC51653
0.7444	Intermediate Similarity	NPC474232
0.7444	Intermediate Similarity	NPC473455
0.7444	Intermediate Similarity	NPC179394
0.7442	Intermediate Similarity	NPC169575
0.7442	Intermediate Similarity	NPC59097
0.7442	Intermediate Similarity	NPC40746
0.7439	Intermediate Similarity	NPC235906
0.7419	Intermediate Similarity	NPC17585
0.7416	Intermediate Similarity	NPC475902
0.7416	Intermediate Similarity	NPC469653
0.7416	Intermediate Similarity	NPC475906
0.7416	Intermediate Similarity	NPC476803
0.7416	Intermediate Similarity	NPC475819
0.7416	Intermediate Similarity	NPC476805
0.7416	Intermediate Similarity	NPC471047
0.7416	Intermediate Similarity	NPC469628
0.7416	Intermediate Similarity	NPC469631
0.7412	Intermediate Similarity	NPC24417
0.7412	Intermediate Similarity	NPC42470
0.7407	Intermediate Similarity	NPC117746
0.7407	Intermediate Similarity	NPC15499
0.7407	Intermediate Similarity	NPC474758
0.7407	Intermediate Similarity	NPC294434
0.7407	Intermediate Similarity	NPC259599
0.7396	Intermediate Similarity	NPC149371
0.7391	Intermediate Similarity	NPC471147
0.7386	Intermediate Similarity	NPC472009
0.7386	Intermediate Similarity	NPC107787
0.7381	Intermediate Similarity	NPC167881
0.7381	Intermediate Similarity	NPC98557
0.7381	Intermediate Similarity	NPC471299
0.7381	Intermediate Similarity	NPC99651
0.7381	Intermediate Similarity	NPC617
0.7381	Intermediate Similarity	NPC150646
0.7368	Intermediate Similarity	NPC477512
0.7363	Intermediate Similarity	NPC284185
0.7363	Intermediate Similarity	NPC150978
0.7363	Intermediate Similarity	NPC32944
0.7363	Intermediate Similarity	NPC70595
0.7363	Intermediate Similarity	NPC74103
0.7363	Intermediate Similarity	NPC123177
0.7363	Intermediate Similarity	NPC193396
0.7356	Intermediate Similarity	NPC159635
0.7356	Intermediate Similarity	NPC41856
0.7356	Intermediate Similarity	NPC115786
0.7356	Intermediate Similarity	NPC96259
0.7356	Intermediate Similarity	NPC141193
0.7349	Intermediate Similarity	NPC7563
0.7349	Intermediate Similarity	NPC320630
0.7349	Intermediate Similarity	NPC476794
0.7349	Intermediate Similarity	NPC116177
0.7349	Intermediate Similarity	NPC470240
0.7349	Intermediate Similarity	NPC474760
0.7342	Intermediate Similarity	NPC199557
0.7333	Intermediate Similarity	NPC87306
0.7326	Intermediate Similarity	NPC229825
0.7326	Intermediate Similarity	NPC26624
0.732	Intermediate Similarity	NPC475871
0.732	Intermediate Similarity	NPC475945
0.7312	Intermediate Similarity	NPC214694
0.7312	Intermediate Similarity	NPC471142
0.7312	Intermediate Similarity	NPC475659
0.7312	Intermediate Similarity	NPC477922
0.7308	Intermediate Similarity	NPC203335
0.7303	Intermediate Similarity	NPC231889
0.7303	Intermediate Similarity	NPC300779
0.7303	Intermediate Similarity	NPC23622
0.7303	Intermediate Similarity	NPC160138
0.7294	Intermediate Similarity	NPC302426
0.7292	Intermediate Similarity	NPC47880
0.7292	Intermediate Similarity	NPC164598
0.7292	Intermediate Similarity	NPC46998
0.7292	Intermediate Similarity	NPC128733
0.7292	Intermediate Similarity	NPC185141
0.7292	Intermediate Similarity	NPC133907
0.7292	Intermediate Similarity	NPC474339
0.7292	Intermediate Similarity	NPC110443
0.7284	Intermediate Similarity	NPC472956
0.7283	Intermediate Similarity	NPC295204
0.7283	Intermediate Similarity	NPC162205
0.7283	Intermediate Similarity	NPC273579
0.7283	Intermediate Similarity	NPC288240
0.7273	Intermediate Similarity	NPC21469
0.7273	Intermediate Similarity	NPC261380
0.7273	Intermediate Similarity	NPC50362
0.7273	Intermediate Similarity	NPC78089
0.7273	Intermediate Similarity	NPC165162
0.7273	Intermediate Similarity	NPC11804
0.7273	Intermediate Similarity	NPC319795
0.7273	Intermediate Similarity	NPC38468
0.7263	Intermediate Similarity	NPC471144
0.7263	Intermediate Similarity	NPC208233
0.7262	Intermediate Similarity	NPC196653
0.7262	Intermediate Similarity	NPC471465
0.7253	Intermediate Similarity	NPC62815
0.7253	Intermediate Similarity	NPC473619
0.7253	Intermediate Similarity	NPC253144
0.7253	Intermediate Similarity	NPC475748
0.7253	Intermediate Similarity	NPC166554
0.7253	Intermediate Similarity	NPC475855
0.725	Intermediate Similarity	NPC472017
0.725	Intermediate Similarity	NPC69462
0.7245	Intermediate Similarity	NPC146731
0.7245	Intermediate Similarity	NPC296950
0.7245	Intermediate Similarity	NPC474741
0.7241	Intermediate Similarity	NPC473390
0.7241	Intermediate Similarity	NPC39588
0.7241	Intermediate Similarity	NPC250315

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 NPC473981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1936
0.2-0.3	4045
0.3-0.4	2111
0.4-0.5	614
0.5-0.6	240
0.6-0.7	32
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7471	Intermediate Similarity	NPD1694	Approved
0.7273	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5209	Approved
0.7065	Intermediate Similarity	NPD5785	Approved
0.6907	Remote Similarity	NPD4225	Approved
0.6889	Remote Similarity	NPD5363	Approved
0.6765	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6698	Approved
0.6702	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6629	Remote Similarity	NPD5369	Approved
0.6625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1695	Approved
0.6571	Remote Similarity	NPD6371	Approved
0.6556	Remote Similarity	NPD4269	Approved
0.6556	Remote Similarity	NPD4270	Approved
0.6556	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4252	Approved
0.6512	Remote Similarity	NPD8039	Approved
0.6452	Remote Similarity	NPD5786	Approved
0.64	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7838	Discovery
0.6333	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5282	Discontinued
0.6304	Remote Similarity	NPD7154	Phase 3
0.6289	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD5370	Suspended
0.6224	Remote Similarity	NPD5779	Approved
0.6224	Remote Similarity	NPD5778	Approved
0.618	Remote Similarity	NPD4756	Discovery
0.6154	Remote Similarity	NPD4820	Approved
0.6154	Remote Similarity	NPD4819	Approved
0.6154	Remote Similarity	NPD4822	Approved
0.6154	Remote Similarity	NPD4821	Approved
0.6111	Remote Similarity	NPD4268	Approved
0.6111	Remote Similarity	NPD4271	Approved
0.6105	Remote Similarity	NPD4249	Approved
0.6082	Remote Similarity	NPD6101	Approved
0.6082	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4251	Approved
0.6042	Remote Similarity	NPD4250	Approved
0.6034	Remote Similarity	NPD7642	Approved
0.6022	Remote Similarity	NPD6435	Approved
0.6019	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.5981	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD2067	Discontinued
0.5962	Remote Similarity	NPD5344	Discontinued
0.596	Remote Similarity	NPD5693	Phase 1
0.596	Remote Similarity	NPD6411	Approved
0.5957	Remote Similarity	NPD5362	Discontinued
0.5952	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7146	Approved
0.5938	Remote Similarity	NPD7521	Approved
0.5938	Remote Similarity	NPD6409	Approved
0.5938	Remote Similarity	NPD6684	Approved
0.5938	Remote Similarity	NPD7334	Approved
0.5938	Remote Similarity	NPD5330	Approved
0.5934	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6686	Approved
0.5882	Remote Similarity	NPD7839	Suspended
0.5859	Remote Similarity	NPD5207	Approved
0.5833	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5737	Approved
0.5816	Remote Similarity	NPD6672	Approved
0.5816	Remote Similarity	NPD6903	Approved
0.5816	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5368	Approved
0.58	Remote Similarity	NPD7637	Suspended
0.5789	Remote Similarity	NPD6110	Phase 1
0.5784	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5695	Phase 3
0.5783	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5696	Approved
0.5766	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD7331	Phase 2
0.575	Remote Similarity	NPD8074	Phase 3
0.5743	Remote Similarity	NPD6399	Phase 3
0.5741	Remote Similarity	NPD6008	Approved
0.5727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6053	Discontinued
0.5714	Remote Similarity	NPD8297	Approved
0.5714	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3573	Approved
0.5688	Remote Similarity	NPD5697	Approved
0.5686	Remote Similarity	NPD7900	Approved
0.5686	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6084	Phase 2
0.5673	Remote Similarity	NPD6083	Phase 2
0.567	Remote Similarity	NPD1696	Phase 3
0.5652	Remote Similarity	NPD7500	Approved
0.5644	Remote Similarity	NPD5694	Approved
0.5641	Remote Similarity	NPD6319	Approved
0.5636	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6899	Approved
0.5636	Remote Similarity	NPD6881	Approved
0.563	Remote Similarity	NPD7829	Approved
0.563	Remote Similarity	NPD7830	Approved
0.5625	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6650	Approved
0.5625	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD5332	Approved
0.5625	Remote Similarity	NPD5331	Approved
0.5625	Remote Similarity	NPD2204	Approved
0.5619	Remote Similarity	NPD7638	Approved
0.5612	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6080	Approved
0.56	Remote Similarity	NPD6904	Approved
0.56	Remote Similarity	NPD6051	Approved
0.56	Remote Similarity	NPD6673	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