NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	257.918
LogP:	4.074
LogD:	3.901
LogS:	-4.104
# Rotatable Bonds:	2
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.779
Synthetic Accessibility Score:	4.589
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.76
MDCK Permeability:	2.6020585210062563e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.317
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	95.78821563720703%
Volume Distribution (VD):	1.418
Pgp-substrate:	4.657402038574219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.163
CYP1A2-substrate:	0.897
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.817
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.844
CYP3A4-inhibitor:	0.304
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	2.5
Half-life (T1/2):	0.348

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.376
Skin Sensitization:	0.185
Carcinogencity:	0.228
Eye Corrosion:	0.016
Eye Irritation:	0.229
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC184737

Natural Product ID:	NPC184737
*Common Name:**	(6R,7R,7As)-6-Ethenyl-3,6-Dimethyl-7-Prop-1-En-2-Yl-4,5,7,7A-Tetrahydro-1-Benzofuran-2-One
IUPAC Name:	(6R,7R,7aS)-6-ethenyl-3,6-dimethyl-7-prop-1-en-2-yl-4,5,7,7a-tetrahydro-1-benzofuran-2-one
Synonyms:
Standard InCHIKey:	GXRBKDQCWNWEHB-GUTXKFCHSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-6-15(5)8-7-11-10(4)14(16)17-13(11)12(15)9(2)3/h6,12-13H,1-2,7-8H2,3-5H3/t12-,13+,15-/m0/s1
SMILES:	C=C[C@@]1(C)CCC2=C(C)C(=O)O[C@H]2[C@@H]1C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449553
PubChem CID:	11572187
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
NPO32969	eunicea sp.	Species	Plexauridae	Eukaryota	n.a.	Caribbean gorgonian coral	n.a.	PMID[16180813]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	50.0	ug.mL-1	PMID[491950]

☑ 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 NPC184737 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	174
0.1-0.2	1131
0.2-0.3	4790
0.3-0.4	13901
0.4-0.5	10675
0.5-0.6	7529
0.6-0.7	3769
0.7-0.8	684
0.8-0.85	37
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9067	High Similarity	NPC189206
0.8961	High Similarity	NPC268827
0.875	High Similarity	NPC96055
0.8571	High Similarity	NPC310479
0.85	High Similarity	NPC471218
0.8434	Intermediate Similarity	NPC473891
0.8415	Intermediate Similarity	NPC474013
0.8415	Intermediate Similarity	NPC471795
0.8395	Intermediate Similarity	NPC474193
0.8395	Intermediate Similarity	NPC12283
0.8395	Intermediate Similarity	NPC193198
0.8372	Intermediate Similarity	NPC152778
0.8372	Intermediate Similarity	NPC162615
0.8372	Intermediate Similarity	NPC205034
0.8353	Intermediate Similarity	NPC221111
0.8353	Intermediate Similarity	NPC280149
0.8353	Intermediate Similarity	NPC182136
0.8333	Intermediate Similarity	NPC215831
0.8333	Intermediate Similarity	NPC54996
0.8313	Intermediate Similarity	NPC131813
0.8235	Intermediate Similarity	NPC73995
0.8193	Intermediate Similarity	NPC177932
0.8171	Intermediate Similarity	NPC30502
0.8171	Intermediate Similarity	NPC311070
0.8171	Intermediate Similarity	NPC472377
0.8148	Intermediate Similarity	NPC38642
0.814	Intermediate Similarity	NPC8062
0.814	Intermediate Similarity	NPC78973
0.8118	Intermediate Similarity	NPC477128
0.8118	Intermediate Similarity	NPC93411
0.8108	Intermediate Similarity	NPC472266
0.8095	Intermediate Similarity	NPC471219
0.809	Intermediate Similarity	NPC473153
0.809	Intermediate Similarity	NPC16967
0.8072	Intermediate Similarity	NPC32223
0.8072	Intermediate Similarity	NPC30486
0.8068	Intermediate Similarity	NPC191521
0.8068	Intermediate Similarity	NPC477130
0.8068	Intermediate Similarity	NPC477129
0.8052	Intermediate Similarity	NPC16349
0.8052	Intermediate Similarity	NPC222244
0.8049	Intermediate Similarity	NPC200513
0.8046	Intermediate Similarity	NPC472953
0.8046	Intermediate Similarity	NPC472811
0.8046	Intermediate Similarity	NPC72845
0.8026	Intermediate Similarity	NPC469660
0.8025	Intermediate Similarity	NPC10636
0.8025	Intermediate Similarity	NPC233332
0.8023	Intermediate Similarity	NPC177141
0.8023	Intermediate Similarity	NPC50488
0.8023	Intermediate Similarity	NPC474396
0.8	Intermediate Similarity	NPC312561
0.8	Intermediate Similarity	NPC471220
0.8	Intermediate Similarity	NPC471796
0.8	Intermediate Similarity	NPC476600
0.7976	Intermediate Similarity	NPC189311
0.7975	Intermediate Similarity	NPC4509
0.7973	Intermediate Similarity	NPC116013
0.7955	Intermediate Similarity	NPC472812
0.7955	Intermediate Similarity	NPC139692
0.7955	Intermediate Similarity	NPC53555
0.7952	Intermediate Similarity	NPC22611
0.7952	Intermediate Similarity	NPC222358
0.7952	Intermediate Similarity	NPC321385
0.7952	Intermediate Similarity	NPC474809
0.7931	Intermediate Similarity	NPC152467
0.7931	Intermediate Similarity	NPC273199
0.7927	Intermediate Similarity	NPC170303
0.7927	Intermediate Similarity	NPC475944
0.7927	Intermediate Similarity	NPC25554
0.7927	Intermediate Similarity	NPC475665
0.7912	Intermediate Similarity	NPC474440
0.7907	Intermediate Similarity	NPC473879
0.7907	Intermediate Similarity	NPC226863
0.7895	Intermediate Similarity	NPC265574
0.7889	Intermediate Similarity	NPC165632
0.7882	Intermediate Similarity	NPC329692
0.7875	Intermediate Similarity	NPC41780
0.7875	Intermediate Similarity	NPC187568
0.7875	Intermediate Similarity	NPC316500
0.7865	Intermediate Similarity	NPC84893
0.7865	Intermediate Similarity	NPC38830
0.7865	Intermediate Similarity	NPC470255
0.7865	Intermediate Similarity	NPC161998
0.7865	Intermediate Similarity	NPC57117
0.7857	Intermediate Similarity	NPC149869
0.7857	Intermediate Similarity	NPC474693
0.7857	Intermediate Similarity	NPC475100
0.7841	Intermediate Similarity	NPC329842
0.7831	Intermediate Similarity	NPC256112
0.7831	Intermediate Similarity	NPC178676
0.7816	Intermediate Similarity	NPC288699
0.7805	Intermediate Similarity	NPC195424
0.7805	Intermediate Similarity	NPC469802
0.7802	Intermediate Similarity	NPC84335
0.7802	Intermediate Similarity	NPC205143
0.7802	Intermediate Similarity	NPC38530
0.7802	Intermediate Similarity	NPC110937
0.7778	Intermediate Similarity	NPC183012
0.7778	Intermediate Similarity	NPC276110
0.7765	Intermediate Similarity	NPC472442
0.7765	Intermediate Similarity	NPC106416
0.7765	Intermediate Similarity	NPC65661
0.7765	Intermediate Similarity	NPC473659
0.7765	Intermediate Similarity	NPC30984
0.7765	Intermediate Similarity	NPC86316
0.7765	Intermediate Similarity	NPC476678
0.7765	Intermediate Similarity	NPC475860
0.7765	Intermediate Similarity	NPC474694
0.7763	Intermediate Similarity	NPC276290
0.7753	Intermediate Similarity	NPC475657
0.7753	Intermediate Similarity	NPC7349
0.7738	Intermediate Similarity	NPC477124
0.7738	Intermediate Similarity	NPC23748
0.7738	Intermediate Similarity	NPC49208
0.7738	Intermediate Similarity	NPC472440
0.7738	Intermediate Similarity	NPC42476
0.7727	Intermediate Similarity	NPC281942
0.7727	Intermediate Similarity	NPC232426
0.7727	Intermediate Similarity	NPC220454
0.7727	Intermediate Similarity	NPC302280
0.7727	Intermediate Similarity	NPC469595
0.7727	Intermediate Similarity	NPC212679
0.7711	Intermediate Similarity	NPC282293
0.7711	Intermediate Similarity	NPC159148
0.7711	Intermediate Similarity	NPC325031
0.7701	Intermediate Similarity	NPC106332
0.7701	Intermediate Similarity	NPC472810
0.7701	Intermediate Similarity	NPC472378
0.7701	Intermediate Similarity	NPC472809
0.7692	Intermediate Similarity	NPC134072
0.7692	Intermediate Similarity	NPC234993
0.7692	Intermediate Similarity	NPC260796
0.7692	Intermediate Similarity	NPC209297
0.7692	Intermediate Similarity	NPC257618
0.7692	Intermediate Similarity	NPC242848
0.7692	Intermediate Similarity	NPC475380
0.7683	Intermediate Similarity	NPC150646
0.7683	Intermediate Similarity	NPC471299
0.7683	Intermediate Similarity	NPC242767
0.7674	Intermediate Similarity	NPC286153
0.7674	Intermediate Similarity	NPC220478
0.7667	Intermediate Similarity	NPC140277
0.7667	Intermediate Similarity	NPC470697
0.7667	Intermediate Similarity	NPC105490
0.7654	Intermediate Similarity	NPC262747
0.7654	Intermediate Similarity	NPC473825
0.7647	Intermediate Similarity	NPC139566
0.7647	Intermediate Similarity	NPC471302
0.7647	Intermediate Similarity	NPC306951
0.7647	Intermediate Similarity	NPC318515
0.764	Intermediate Similarity	NPC473944
0.764	Intermediate Similarity	NPC303697
0.764	Intermediate Similarity	NPC177037
0.764	Intermediate Similarity	NPC472814
0.764	Intermediate Similarity	NPC141831
0.764	Intermediate Similarity	NPC49420
0.764	Intermediate Similarity	NPC233345
0.764	Intermediate Similarity	NPC186363
0.7634	Intermediate Similarity	NPC474012
0.7634	Intermediate Similarity	NPC476299
0.7632	Intermediate Similarity	NPC474477
0.7619	Intermediate Similarity	NPC226988
0.7619	Intermediate Similarity	NPC35556
0.7619	Intermediate Similarity	NPC268122
0.7619	Intermediate Similarity	NPC16321
0.7619	Intermediate Similarity	NPC94200
0.7619	Intermediate Similarity	NPC186276
0.7614	Intermediate Similarity	NPC284561
0.7614	Intermediate Similarity	NPC5509
0.7614	Intermediate Similarity	NPC470734
0.7614	Intermediate Similarity	NPC82876
0.7609	Intermediate Similarity	NPC100912
0.7609	Intermediate Similarity	NPC475446
0.7609	Intermediate Similarity	NPC73911
0.7609	Intermediate Similarity	NPC311241
0.76	Intermediate Similarity	NPC182794
0.759	Intermediate Similarity	NPC281880
0.7586	Intermediate Similarity	NPC166857
0.7582	Intermediate Similarity	NPC472441
0.7582	Intermediate Similarity	NPC295347
0.7582	Intermediate Similarity	NPC33473
0.7582	Intermediate Similarity	NPC474909
0.7582	Intermediate Similarity	NPC209355
0.7582	Intermediate Similarity	NPC281134
0.7579	Intermediate Similarity	NPC23584
0.7561	Intermediate Similarity	NPC253749
0.7561	Intermediate Similarity	NPC209135
0.7561	Intermediate Similarity	NPC128276
0.7561	Intermediate Similarity	NPC474005
0.7561	Intermediate Similarity	NPC35574
0.7561	Intermediate Similarity	NPC299235
0.7561	Intermediate Similarity	NPC474816
0.7558	Intermediate Similarity	NPC35933
0.7558	Intermediate Similarity	NPC33570
0.7558	Intermediate Similarity	NPC52628
0.7558	Intermediate Similarity	NPC110405
0.7558	Intermediate Similarity	NPC473251
0.7558	Intermediate Similarity	NPC42586
0.7558	Intermediate Similarity	NPC476602

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 NPC184737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1396
0.2-0.3	3974
0.3-0.4	2421
0.4-0.5	808
0.5-0.6	309
0.6-0.7	84
0.7-0.8	3
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
0.8193	Intermediate Similarity	NPD1694	Approved
0.8049	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4225	Approved
0.7368	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7638	Approved
0.7263	Intermediate Similarity	NPD7640	Approved
0.7263	Intermediate Similarity	NPD7639	Approved
0.7209	Intermediate Similarity	NPD5209	Approved
0.7195	Intermediate Similarity	NPD8039	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD7334	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7045	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6051	Approved
0.7013	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6648	Approved
0.6842	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5344	Discontinued
0.6813	Remote Similarity	NPD3573	Approved
0.6774	Remote Similarity	NPD5785	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD6672	Approved
0.6737	Remote Similarity	NPD7900	Approved
0.6737	Remote Similarity	NPD7748	Approved
0.6737	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7637	Suspended
0.6702	Remote Similarity	NPD5693	Phase 1
0.6602	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD7632	Discontinued
0.6596	Remote Similarity	NPD7838	Discovery
0.6574	Remote Similarity	NPD7115	Discovery
0.6531	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD7515	Phase 2
0.6526	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD3618	Phase 1
0.6505	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1695	Approved
0.6458	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD5779	Approved
0.6458	Remote Similarity	NPD6399	Phase 3
0.6421	Remote Similarity	NPD5207	Approved
0.6421	Remote Similarity	NPD6698	Approved
0.6421	Remote Similarity	NPD46	Approved
0.6413	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6001	Approved
0.6383	Remote Similarity	NPD5208	Approved
0.6381	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7154	Phase 3
0.6374	Remote Similarity	NPD5362	Discontinued
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6079	Approved
0.6354	Remote Similarity	NPD5694	Approved
0.6346	Remote Similarity	NPD5697	Approved
0.6329	Remote Similarity	NPD4192	Approved
0.6329	Remote Similarity	NPD4193	Approved
0.6329	Remote Similarity	NPD4194	Approved
0.6329	Remote Similarity	NPD4191	Approved
0.6327	Remote Similarity	NPD5695	Phase 3
0.6321	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5328	Approved
0.6316	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD6904	Approved
0.6316	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6080	Approved
0.6316	Remote Similarity	NPD6673	Approved
0.6304	Remote Similarity	NPD3133	Approved
0.6304	Remote Similarity	NPD3666	Approved
0.6304	Remote Similarity	NPD3665	Phase 1
0.6286	Remote Similarity	NPD6899	Approved
0.6286	Remote Similarity	NPD6011	Approved
0.6286	Remote Similarity	NPD6881	Approved
0.6279	Remote Similarity	NPD6926	Approved
0.6279	Remote Similarity	NPD6924	Approved
0.6264	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD5692	Phase 3
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7128	Approved
0.6237	Remote Similarity	NPD5363	Approved
0.6226	Remote Similarity	NPD6013	Approved
0.6226	Remote Similarity	NPD6012	Approved
0.6226	Remote Similarity	NPD6014	Approved
0.6222	Remote Similarity	NPD4822	Approved
0.6222	Remote Similarity	NPD4820	Approved
0.6222	Remote Similarity	NPD4821	Approved
0.6222	Remote Similarity	NPD4819	Approved
0.6216	Remote Similarity	NPD7328	Approved
0.6216	Remote Similarity	NPD7327	Approved
0.6207	Remote Similarity	NPD8264	Approved
0.62	Remote Similarity	NPD6083	Phase 2
0.62	Remote Similarity	NPD6084	Phase 2
0.6196	Remote Similarity	NPD5332	Approved
0.6196	Remote Similarity	NPD6695	Phase 3
0.6196	Remote Similarity	NPD5331	Approved
0.6195	Remote Similarity	NPD8033	Approved
0.619	Remote Similarity	NPD5701	Approved
0.6186	Remote Similarity	NPD6050	Approved
0.618	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4271	Approved
0.618	Remote Similarity	NPD4268	Approved
0.617	Remote Similarity	NPD6098	Approved
0.617	Remote Similarity	NPD4519	Discontinued
0.617	Remote Similarity	NPD4623	Approved
0.617	Remote Similarity	NPD5279	Phase 3
0.6168	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD7290	Approved
0.6168	Remote Similarity	NPD7102	Approved
0.6161	Remote Similarity	NPD7516	Approved
0.6154	Remote Similarity	NPD4790	Discontinued
0.6139	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5696	Approved
0.6136	Remote Similarity	NPD6933	Approved
0.6136	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7320	Approved
0.6129	Remote Similarity	NPD3668	Phase 3
0.6129	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4786	Approved
0.6122	Remote Similarity	NPD4202	Approved
0.6118	Remote Similarity	NPD7143	Approved
0.6118	Remote Similarity	NPD7144	Approved
0.6111	Remote Similarity	NPD6649	Approved
0.6111	Remote Similarity	NPD6869	Approved
0.6111	Remote Similarity	NPD6929	Approved
0.6111	Remote Similarity	NPD6617	Approved
0.6111	Remote Similarity	NPD4195	Approved
0.6111	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD7645	Phase 2
0.6111	Remote Similarity	NPD6847	Approved
0.6111	Remote Similarity	NPD8130	Phase 1
0.6106	Remote Similarity	NPD8377	Approved
0.6106	Remote Similarity	NPD8294	Approved
0.61	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5222	Approved
0.61	Remote Similarity	NPD5221	Approved
0.6087	Remote Similarity	NPD4270	Approved
0.6087	Remote Similarity	NPD4269	Approved
0.6075	Remote Similarity	NPD6373	Approved
0.6075	Remote Similarity	NPD6372	Approved
0.6064	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1696	Phase 3
0.6061	Remote Similarity	NPD5282	Discontinued
0.6055	Remote Similarity	NPD6882	Approved
0.6055	Remote Similarity	NPD8297	Approved
0.6053	Remote Similarity	NPD7503	Approved
0.6053	Remote Similarity	NPD8296	Approved
0.6053	Remote Similarity	NPD8379	Approved
0.6053	Remote Similarity	NPD8378	Approved
0.6053	Remote Similarity	NPD8380	Approved
0.6053	Remote Similarity	NPD8335	Approved
0.6047	Remote Similarity	NPD7150	Approved
0.6047	Remote Similarity	NPD7151	Approved
0.6047	Remote Similarity	NPD7152	Approved
0.6044	Remote Similarity	NPD4695	Discontinued
0.6044	Remote Similarity	NPD7509	Discontinued
0.6044	Remote Similarity	NPD7514	Phase 3
0.6044	Remote Similarity	NPD6930	Phase 2
0.6044	Remote Similarity	NPD7332	Phase 2
0.6044	Remote Similarity	NPD7525	Registered
0.6044	Remote Similarity	NPD6931	Approved
0.604	Remote Similarity	NPD5173	Approved
0.6023	Remote Similarity	NPD7339	Approved
0.6023	Remote Similarity	NPD6942	Approved
0.602	Remote Similarity	NPD8034	Phase 2
0.602	Remote Similarity	NPD5281	Approved
0.602	Remote Similarity	NPD5284	Approved
0.602	Remote Similarity	NPD8035	Phase 2
0.6019	Remote Similarity	NPD6371	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD6922	Approved
0.6	Remote Similarity	NPD6923	Approved
0.6	Remote Similarity	NPD5786	Approved
0.5983	Remote Similarity	NPD7507	Approved
0.5978	Remote Similarity	NPD5369	Approved
0.5978	Remote Similarity	NPD6902	Approved
0.5963	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5211	Phase 2
0.5941	Remote Similarity	NPD4697	Phase 3
0.5938	Remote Similarity	NPD4250	Approved
0.5938	Remote Similarity	NPD4251	Approved
0.5938	Remote Similarity	NPD7750	Discontinued
0.5938	Remote Similarity	NPD7524	Approved
0.5926	Remote Similarity	NPD368	Approved
0.5922	Remote Similarity	NPD5286	Approved
0.5922	Remote Similarity	NPD4696	Approved
0.5922	Remote Similarity	NPD5285	Approved
0.5914	Remote Similarity	NPD4223	Phase 3
0.5914	Remote Similarity	NPD6435	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