NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.17
Volume:	251.764
LogP:	4.209
LogD:	4.378
LogS:	-4.851
# Rotatable Bonds:	3
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	3.852
Fsp3:	0.6
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:	-4.496
MDCK Permeability:	2.009355193877127e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.122
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.212
Plasma Protein Binding (PPB):	96.15824127197266%
Volume Distribution (VD):	2.132
Pgp-substrate:	2.5805294513702393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.868
CYP1A2-substrate:	0.728
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.343
CYP2C9-inhibitor:	0.523
CYP2C9-substrate:	0.533
CYP2D6-inhibitor:	0.683
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.578
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	9.916
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.785
Maximum Recommended Daily Dose:	0.353
Skin Sensitization:	0.16
Carcinogencity:	0.71
Eye Corrosion:	0.855
Eye Irritation:	0.981
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC150895

Natural Product ID:	NPC150895
*Common Name:**	Microcionin-4
IUPAC Name:	3-[2-[(1R,2R)-1,2-dimethyl-6-methylidenecyclohexyl]ethyl]furan
Synonyms:	Microcionin-4
Standard InCHIKey:	VFZHDBFYTSLCHG-HIFRSBDPSA-N
Standard InCHI:	InChI=1S/C15H22O/c1-12-5-4-6-13(2)15(12,3)9-7-14-8-10-16-11-14/h8,10-11,13H,1,4-7,9H2,2-3H3/t13-,15+/m1/s1
SMILES:	C=C1CCC[C@@H](C)[C@@]1(C)CCc1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469255
PubChem CID:	21778335
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004144] Heteroaromatic compounds

*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
NPO12901	Dysidea septosa	Species	Dysideidae	Eukaryota	n.a.	Hainan, China	n.a.	PMID[18627201]
NPO12901	Dysidea septosa	Species	Dysideidae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	6.8	ug.mL-1	PMID[538569]

☑ 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 NPC150895 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	356
0.1-0.2	1528
0.2-0.3	3738
0.3-0.4	10604
0.4-0.5	10837
0.5-0.6	11162
0.6-0.7	3938
0.7-0.8	428
0.8-0.85	69
0.85-0.9	27
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9304	High Similarity	NPC16922
0.9145	High Similarity	NPC179354
0.9068	High Similarity	NPC46536
0.9068	High Similarity	NPC23086
0.9068	High Similarity	NPC138139
0.9068	High Similarity	NPC74612
0.9052	High Similarity	NPC317217
0.9052	High Similarity	NPC477967
0.9035	High Similarity	NPC243704
0.8983	High Similarity	NPC473885
0.8983	High Similarity	NPC471074
0.8947	High Similarity	NPC212918
0.8917	High Similarity	NPC207294
0.8917	High Similarity	NPC477966
0.8917	High Similarity	NPC327527
0.8917	High Similarity	NPC112706
0.8917	High Similarity	NPC476917
0.8917	High Similarity	NPC477123
0.8917	High Similarity	NPC477040
0.8898	High Similarity	NPC477965
0.8898	High Similarity	NPC477038
0.8843	High Similarity	NPC59502
0.8833	High Similarity	NPC83178
0.8803	High Similarity	NPC97566
0.877	High Similarity	NPC476925
0.876	High Similarity	NPC477039
0.8739	High Similarity	NPC243269
0.8699	High Similarity	NPC61788
0.8699	High Similarity	NPC89133
0.8621	High Similarity	NPC144745
0.8621	High Similarity	NPC208906
0.8609	High Similarity	NPC28054
0.8571	High Similarity	NPC36255
0.856	High Similarity	NPC218838
0.856	High Similarity	NPC471006
0.8548	High Similarity	NPC298190
0.8534	High Similarity	NPC45536
0.8525	High Similarity	NPC95567
0.8525	High Similarity	NPC319140
0.85	High Similarity	NPC272899
0.848	Intermediate Similarity	NPC471817
0.8475	Intermediate Similarity	NPC137710
0.843	Intermediate Similarity	NPC130275
0.843	Intermediate Similarity	NPC188377
0.843	Intermediate Similarity	NPC178382
0.843	Intermediate Similarity	NPC65735
0.843	Intermediate Similarity	NPC83115
0.843	Intermediate Similarity	NPC118853
0.8425	Intermediate Similarity	NPC476947
0.8425	Intermediate Similarity	NPC158525
0.8421	Intermediate Similarity	NPC105249
0.8421	Intermediate Similarity	NPC277525
0.839	Intermediate Similarity	NPC87466
0.8376	Intermediate Similarity	NPC79202
0.8376	Intermediate Similarity	NPC59035
0.8374	Intermediate Similarity	NPC290955
0.8374	Intermediate Similarity	NPC246392
0.8361	Intermediate Similarity	NPC303010
0.8361	Intermediate Similarity	NPC230979
0.8359	Intermediate Similarity	NPC46896
0.8359	Intermediate Similarity	NPC146872
0.8333	Intermediate Similarity	NPC473982
0.8319	Intermediate Similarity	NPC473969
0.8319	Intermediate Similarity	NPC471521
0.8319	Intermediate Similarity	NPC473356
0.8306	Intermediate Similarity	NPC329707
0.8306	Intermediate Similarity	NPC26532
0.8295	Intermediate Similarity	NPC307401
0.8295	Intermediate Similarity	NPC310830
0.8295	Intermediate Similarity	NPC42400
0.8291	Intermediate Similarity	NPC205523
0.8281	Intermediate Similarity	NPC92941
0.8268	Intermediate Similarity	NPC470740
0.8246	Intermediate Similarity	NPC177331
0.824	Intermediate Similarity	NPC208389
0.8231	Intermediate Similarity	NPC476943
0.819	Intermediate Similarity	NPC22678
0.8182	Intermediate Similarity	NPC79557
0.8175	Intermediate Similarity	NPC21460
0.8168	Intermediate Similarity	NPC202260
0.8168	Intermediate Similarity	NPC90953
0.816	Intermediate Similarity	NPC279877
0.8154	Intermediate Similarity	NPC470742
0.8151	Intermediate Similarity	NPC131801
0.8151	Intermediate Similarity	NPC217180
0.8151	Intermediate Similarity	NPC312525
0.8125	Intermediate Similarity	NPC293253
0.8115	Intermediate Similarity	NPC471549
0.8115	Intermediate Similarity	NPC473379
0.8106	Intermediate Similarity	NPC56197
0.8106	Intermediate Similarity	NPC67003
0.8095	Intermediate Similarity	NPC120836
0.8095	Intermediate Similarity	NPC223063
0.8095	Intermediate Similarity	NPC198904
0.8092	Intermediate Similarity	NPC220094
0.8092	Intermediate Similarity	NPC472376
0.8092	Intermediate Similarity	NPC236532
0.8083	Intermediate Similarity	NPC206007
0.808	Intermediate Similarity	NPC476016
0.8065	Intermediate Similarity	NPC300098
0.8065	Intermediate Similarity	NPC71274
0.8065	Intermediate Similarity	NPC290193
0.8065	Intermediate Similarity	NPC75557
0.8065	Intermediate Similarity	NPC474829
0.8045	Intermediate Similarity	NPC205765
0.8034	Intermediate Similarity	NPC1811
0.8034	Intermediate Similarity	NPC26157
0.8033	Intermediate Similarity	NPC115859
0.8016	Intermediate Similarity	NPC474279
0.8016	Intermediate Similarity	NPC474438
0.8015	Intermediate Similarity	NPC215109
0.8015	Intermediate Similarity	NPC170604
0.8	Intermediate Similarity	NPC329922
0.8	Intermediate Similarity	NPC329694
0.8	Intermediate Similarity	NPC83301
0.8	Intermediate Similarity	NPC474260
0.8	Intermediate Similarity	NPC209858
0.8	Intermediate Similarity	NPC81912
0.7985	Intermediate Similarity	NPC473152
0.7985	Intermediate Similarity	NPC263337
0.7985	Intermediate Similarity	NPC52412
0.7985	Intermediate Similarity	NPC121158
0.7982	Intermediate Similarity	NPC42471
0.797	Intermediate Similarity	NPC90296
0.797	Intermediate Similarity	NPC148374
0.7969	Intermediate Similarity	NPC477645
0.7937	Intermediate Similarity	NPC141059
0.7937	Intermediate Similarity	NPC474830
0.7926	Intermediate Similarity	NPC243577
0.7926	Intermediate Similarity	NPC476946
0.7926	Intermediate Similarity	NPC267632
0.7926	Intermediate Similarity	NPC223415
0.792	Intermediate Similarity	NPC471559
0.791	Intermediate Similarity	NPC20500
0.7907	Intermediate Similarity	NPC471995
0.7903	Intermediate Similarity	NPC476351
0.7886	Intermediate Similarity	NPC1848
0.7879	Intermediate Similarity	NPC186626
0.7868	Intermediate Similarity	NPC476944
0.7868	Intermediate Similarity	NPC251865
0.7868	Intermediate Similarity	NPC142113
0.7868	Intermediate Similarity	NPC238843
0.7868	Intermediate Similarity	NPC199044
0.7863	Intermediate Similarity	NPC324117
0.7857	Intermediate Similarity	NPC470858
0.7851	Intermediate Similarity	NPC227660
0.7846	Intermediate Similarity	NPC474407
0.7846	Intermediate Similarity	NPC474425
0.7846	Intermediate Similarity	NPC474426
0.7836	Intermediate Similarity	NPC473983
0.7836	Intermediate Similarity	NPC201370
0.7823	Intermediate Similarity	NPC263870
0.7823	Intermediate Similarity	NPC289911
0.7823	Intermediate Similarity	NPC283284
0.782	Intermediate Similarity	NPC177262
0.781	Intermediate Similarity	NPC5676
0.781	Intermediate Similarity	NPC185456
0.7805	Intermediate Similarity	NPC246214
0.7795	Intermediate Similarity	NPC137570
0.7794	Intermediate Similarity	NPC470741
0.7786	Intermediate Similarity	NPC106247
0.7786	Intermediate Similarity	NPC471998
0.7769	Intermediate Similarity	NPC471544
0.7769	Intermediate Similarity	NPC473344
0.7761	Intermediate Similarity	NPC233707
0.776	Intermediate Similarity	NPC475818
0.7759	Intermediate Similarity	NPC140688
0.7754	Intermediate Similarity	NPC346
0.7754	Intermediate Similarity	NPC262198
0.7754	Intermediate Similarity	NPC471292
0.7754	Intermediate Similarity	NPC470999
0.7754	Intermediate Similarity	NPC276676
0.775	Intermediate Similarity	NPC252004
0.7742	Intermediate Similarity	NPC474136
0.7698	Intermediate Similarity	NPC10088
0.7698	Intermediate Similarity	NPC221809
0.7698	Intermediate Similarity	NPC11799
0.7698	Intermediate Similarity	NPC250228
0.7698	Intermediate Similarity	NPC476938
0.7698	Intermediate Similarity	NPC470941
0.7698	Intermediate Similarity	NPC255414
0.7698	Intermediate Similarity	NPC471174
0.7698	Intermediate Similarity	NPC302987
0.7698	Intermediate Similarity	NPC476937
0.7698	Intermediate Similarity	NPC141252
0.7698	Intermediate Similarity	NPC71821
0.7698	Intermediate Similarity	NPC216755
0.7692	Intermediate Similarity	NPC475092
0.7681	Intermediate Similarity	NPC290038
0.7681	Intermediate Similarity	NPC34056
0.7681	Intermediate Similarity	NPC56731
0.7674	Intermediate Similarity	NPC50583
0.7669	Intermediate Similarity	NPC214572
0.7664	Intermediate Similarity	NPC80635
0.7661	Intermediate Similarity	NPC474817
0.7656	Intermediate Similarity	NPC471501
0.7656	Intermediate Similarity	NPC471554
0.7656	Intermediate Similarity	NPC473355
0.7656	Intermediate Similarity	NPC471573
0.7647	Intermediate Similarity	NPC54626

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 NPC150895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	1036
0.2-0.3	1733
0.3-0.4	2921
0.4-0.5	2015
0.5-0.6	907
0.6-0.7	185
0.7-0.8	7
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
0.7521	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1876	Approved
0.7344	Intermediate Similarity	NPD3972	Approved
0.7329	Intermediate Similarity	NPD5761	Phase 2
0.7329	Intermediate Similarity	NPD5760	Phase 2
0.7266	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1471	Phase 3
0.7083	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5585	Approved
0.7015	Intermediate Similarity	NPD6832	Phase 2
0.7	Intermediate Similarity	NPD2344	Approved
0.6992	Remote Similarity	NPD2798	Approved
0.6977	Remote Similarity	NPD17	Approved
0.6977	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4628	Phase 3
0.6917	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1019	Discontinued
0.6861	Remote Similarity	NPD8032	Phase 2
0.6857	Remote Similarity	NPD2799	Discontinued
0.6829	Remote Similarity	NPD2182	Approved
0.6818	Remote Similarity	NPD1608	Approved
0.6818	Remote Similarity	NPD9717	Approved
0.6812	Remote Similarity	NPD3142	Approved
0.6812	Remote Similarity	NPD3140	Approved
0.6809	Remote Similarity	NPD2796	Approved
0.6806	Remote Similarity	NPD2309	Approved
0.6803	Remote Similarity	NPD920	Approved
0.6803	Remote Similarity	NPD3134	Approved
0.6791	Remote Similarity	NPD2797	Approved
0.6781	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1651	Approved
0.6767	Remote Similarity	NPD4359	Approved
0.6742	Remote Similarity	NPD1281	Approved
0.6736	Remote Similarity	NPD7003	Approved
0.6719	Remote Similarity	NPD7157	Approved
0.6718	Remote Similarity	NPD1778	Approved
0.6691	Remote Similarity	NPD4307	Phase 2
0.6691	Remote Similarity	NPD9494	Approved
0.6689	Remote Similarity	NPD3869	Phase 3
0.6689	Remote Similarity	NPD6280	Approved
0.6689	Remote Similarity	NPD6279	Approved
0.6689	Remote Similarity	NPD3873	Phase 3
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD1243	Approved
0.6643	Remote Similarity	NPD6355	Discontinued
0.6643	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5327	Phase 3
0.6641	Remote Similarity	NPD5691	Approved
0.6639	Remote Similarity	NPD164	Approved
0.662	Remote Similarity	NPD3748	Approved
0.6613	Remote Similarity	NPD1358	Approved
0.6593	Remote Similarity	NPD1283	Approved
0.6583	Remote Similarity	NPD1238	Approved
0.6573	Remote Similarity	NPD1551	Phase 2
0.6571	Remote Similarity	NPD2979	Phase 3
0.6565	Remote Similarity	NPD9545	Approved
0.656	Remote Similarity	NPD2684	Approved
0.6552	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD2313	Discontinued
0.6547	Remote Similarity	NPD3268	Approved
0.6544	Remote Similarity	NPD1203	Approved
0.6543	Remote Similarity	NPD6764	Approved
0.6543	Remote Similarity	NPD6765	Approved
0.6541	Remote Similarity	NPD3496	Discontinued
0.6528	Remote Similarity	NPD2346	Discontinued
0.6525	Remote Similarity	NPD4618	Approved
0.6525	Remote Similarity	NPD4622	Approved
0.6507	Remote Similarity	NPD4110	Phase 3
0.6507	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4308	Phase 3
0.65	Remote Similarity	NPD4870	Approved
0.649	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD919	Approved
0.6474	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3887	Approved
0.6458	Remote Similarity	NPD4477	Approved
0.6458	Remote Similarity	NPD4476	Approved
0.6454	Remote Similarity	NPD4140	Approved
0.6452	Remote Similarity	NPD9697	Approved
0.6447	Remote Similarity	NPD6599	Discontinued
0.6446	Remote Similarity	NPD8434	Phase 2
0.6439	Remote Similarity	NPD1894	Discontinued
0.6434	Remote Similarity	NPD5688	Approved
0.6434	Remote Similarity	NPD5689	Approved
0.6429	Remote Similarity	NPD411	Approved
0.6429	Remote Similarity	NPD3764	Approved
0.6418	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6004	Phase 3
0.6414	Remote Similarity	NPD6005	Phase 3
0.6414	Remote Similarity	NPD6002	Phase 3
0.6414	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD9493	Approved
0.6408	Remote Similarity	NPD1933	Approved
0.6408	Remote Similarity	NPD447	Suspended
0.6395	Remote Similarity	NPD3750	Approved
0.6395	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1247	Approved
0.6391	Remote Similarity	NPD3444	Approved
0.6391	Remote Similarity	NPD3445	Approved
0.6391	Remote Similarity	NPD3443	Approved
0.6386	Remote Similarity	NPD6785	Approved
0.6386	Remote Similarity	NPD6784	Approved
0.6382	Remote Similarity	NPD2649	Approved
0.6382	Remote Similarity	NPD7458	Discontinued
0.6382	Remote Similarity	NPD2651	Approved
0.6377	Remote Similarity	NPD5647	Approved
0.637	Remote Similarity	NPD2897	Discontinued
0.637	Remote Similarity	NPD1549	Phase 2
0.637	Remote Similarity	NPD4534	Discontinued
0.6364	Remote Similarity	NPD9092	Discovery
0.6358	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD7843	Approved
0.6357	Remote Similarity	NPD5535	Approved
0.6352	Remote Similarity	NPD6808	Phase 2
0.6346	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2935	Discontinued
0.6345	Remote Similarity	NPD2438	Suspended
0.6345	Remote Similarity	NPD6100	Approved
0.6345	Remote Similarity	NPD6099	Approved
0.6345	Remote Similarity	NPD2531	Phase 2
0.6343	Remote Similarity	NPD4626	Approved
0.6338	Remote Similarity	NPD1240	Approved
0.6333	Remote Similarity	NPD4662	Approved
0.6333	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4661	Approved
0.6331	Remote Similarity	NPD1712	Approved
0.6329	Remote Similarity	NPD5494	Approved
0.6323	Remote Similarity	NPD7819	Suspended
0.6312	Remote Similarity	NPD6798	Discontinued
0.6304	Remote Similarity	NPD6362	Approved
0.6301	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2353	Approved
0.6301	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2296	Approved
0.6276	Remote Similarity	NPD1510	Phase 2
0.6273	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6799	Approved
0.626	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5958	Discontinued
0.6258	Remote Similarity	NPD7577	Discontinued
0.625	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1607	Approved
0.625	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6653	Approved
0.625	Remote Similarity	NPD6287	Discontinued
0.6241	Remote Similarity	NPD7095	Approved
0.6241	Remote Similarity	NPD5536	Phase 2
0.6231	Remote Similarity	NPD821	Approved
0.6225	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.622	Remote Similarity	NPD290	Approved
0.6216	Remote Similarity	NPD2800	Approved
0.6214	Remote Similarity	NPD454	Approved
0.6212	Remote Similarity	NPD2557	Approved
0.6211	Remote Similarity	NPD3926	Phase 2
0.6204	Remote Similarity	NPD1481	Phase 2
0.6203	Remote Similarity	NPD3749	Approved
0.62	Remote Similarity	NPD7440	Discontinued
0.6197	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD6873	Phase 2
0.6188	Remote Similarity	NPD8127	Discontinued
0.6183	Remote Similarity	NPD5283	Phase 1
0.6181	Remote Similarity	NPD5735	Approved
0.6178	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.617	Remote Similarity	NPD2614	Approved
0.6169	Remote Similarity	NPD3226	Approved
0.6165	Remote Similarity	NPD3596	Phase 2
0.6154	Remote Similarity	NPD6233	Phase 2
0.6154	Remote Similarity	NPD4062	Phase 3
0.6148	Remote Similarity	NPD3024	Approved
0.6148	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD3025	Approved
0.6145	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6559	Discontinued
0.6144	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD968	Approved
0.6139	Remote Similarity	NPD3882	Suspended
0.6139	Remote Similarity	NPD7768	Phase 2
0.6138	Remote Similarity	NPD6353	Approved
0.6136	Remote Similarity	NPD5951	Approved
0.6133	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2354	Approved
0.6131	Remote Similarity	NPD1535	Discovery
0.6131	Remote Similarity	NPD1611	Approved
0.6129	Remote Similarity	NPD7028	Phase 2
0.6127	Remote Similarity	NPD7008	Discontinued
0.6125	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD2067	Discontinued
0.6118	Remote Similarity	NPD2532	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