NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	261.06
Volume:	252.784
LogP:	0.529
LogD:	0.774
LogS:	-3.102
# Rotatable Bonds:	3
TPSA:	90.4
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	3.318
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.667
MDCK Permeability:	3.090195241384208e-05
Pgp-inhibitor:	0.072
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.377
Plasma Protein Binding (PPB):	73.10224151611328%
Volume Distribution (VD):	0.749
Pgp-substrate:	38.347049713134766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.789
CYP1A2-substrate:	0.314
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.119
CYP3A4-substrate:	0.199

ADMET: Excretion

Clearance (CL):	1.788
Half-life (T1/2):	0.442

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.852
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.192
Carcinogencity:	0.331
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.625

Download Data

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

Natural Product: NPC109922

Natural Product ID:	NPC109922
*Common Name:**	FCVLIMJMXLPMSE-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	O-Demethyl Renierol Acetate
Standard InCHIKey:	FCVLIMJMXLPMSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11NO5/c1-6-11(16)8-3-4-14-9(5-19-7(2)15)10(8)13(18)12(6)17/h3-4,17H,5H2,1-2H3
SMILES:	CC1=C(C(=O)c2c(ccnc2COC(=O)C)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491882
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002567] Isoquinoline quinones

*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
NPO3622	Petrosia similis	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346970]
NPO3622	Petrosia similis	Species	Petrosiidae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	14.0	mm	PMID[523120]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	16.0	mm	PMID[523120]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	12.0	mm	PMID[523120]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	12.0	mm	PMID[523120]

☑ 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 NPC109922 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	274
0.1-0.2	1917
0.2-0.3	9039
0.3-0.4	11087
0.4-0.5	15525
0.5-0.6	3308
0.6-0.7	1281
0.7-0.8	256
0.8-0.85	5
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC114974
0.9061	High Similarity	NPC135950
0.8865	High Similarity	NPC103361
0.8533	High Similarity	NPC469489
0.8167	Intermediate Similarity	NPC249614
0.8056	Intermediate Similarity	NPC470894
0.7967	Intermediate Similarity	NPC273532
0.7901	Intermediate Similarity	NPC41717
0.7797	Intermediate Similarity	NPC107287
0.7757	Intermediate Similarity	NPC35208
0.774	Intermediate Similarity	NPC70406
0.7713	Intermediate Similarity	NPC471997
0.7708	Intermediate Similarity	NPC44354
0.7707	Intermediate Similarity	NPC228331
0.7684	Intermediate Similarity	NPC207851
0.7674	Intermediate Similarity	NPC475426
0.767	Intermediate Similarity	NPC477910
0.7667	Intermediate Similarity	NPC76565
0.7644	Intermediate Similarity	NPC282103
0.7642	Intermediate Similarity	NPC146824
0.7635	Intermediate Similarity	NPC48042
0.7635	Intermediate Similarity	NPC472550
0.7635	Intermediate Similarity	NPC304179
0.7635	Intermediate Similarity	NPC472752
0.763	Intermediate Similarity	NPC475137
0.763	Intermediate Similarity	NPC475498
0.7626	Intermediate Similarity	NPC123395
0.7624	Intermediate Similarity	NPC193238
0.7621	Intermediate Similarity	NPC319128
0.7606	Intermediate Similarity	NPC475362
0.7594	Intermediate Similarity	NPC473506
0.7586	Intermediate Similarity	NPC470190
0.7586	Intermediate Similarity	NPC63041
0.7571	Intermediate Similarity	NPC477912
0.7571	Intermediate Similarity	NPC112741
0.7559	Intermediate Similarity	NPC476110
0.7559	Intermediate Similarity	NPC475600
0.7559	Intermediate Similarity	NPC475631
0.7559	Intermediate Similarity	NPC87152
0.7556	Intermediate Similarity	NPC263455
0.7535	Intermediate Similarity	NPC473689
0.7535	Intermediate Similarity	NPC292416
0.7534	Intermediate Similarity	NPC253482
0.7526	Intermediate Similarity	NPC317010
0.7524	Intermediate Similarity	NPC472553
0.7523	Intermediate Similarity	NPC470486
0.7523	Intermediate Similarity	NPC471190
0.7523	Intermediate Similarity	NPC475644
0.7523	Intermediate Similarity	NPC471977
0.75	Intermediate Similarity	NPC320324
0.75	Intermediate Similarity	NPC42678
0.75	Intermediate Similarity	NPC57797
0.75	Intermediate Similarity	NPC250807
0.75	Intermediate Similarity	NPC319880
0.75	Intermediate Similarity	NPC244839
0.75	Intermediate Similarity	NPC79223
0.75	Intermediate Similarity	NPC477909
0.75	Intermediate Similarity	NPC477907
0.7477	Intermediate Similarity	NPC14116
0.7477	Intermediate Similarity	NPC285411
0.7477	Intermediate Similarity	NPC475601
0.7476	Intermediate Similarity	NPC40919
0.7476	Intermediate Similarity	NPC470189
0.7473	Intermediate Similarity	NPC213914
0.7465	Intermediate Similarity	NPC473850
0.7465	Intermediate Similarity	NPC237702
0.7463	Intermediate Similarity	NPC328559
0.7463	Intermediate Similarity	NPC32451
0.7459	Intermediate Similarity	NPC209362
0.7454	Intermediate Similarity	NPC475596
0.7454	Intermediate Similarity	NPC475303
0.7453	Intermediate Similarity	NPC477911
0.7449	Intermediate Similarity	NPC138370
0.7447	Intermediate Similarity	NPC191310
0.7442	Intermediate Similarity	NPC311196
0.7442	Intermediate Similarity	NPC134384
0.7432	Intermediate Similarity	NPC475648
0.7431	Intermediate Similarity	NPC475406
0.743	Intermediate Similarity	NPC148860
0.7429	Intermediate Similarity	NPC62367
0.7419	Intermediate Similarity	NPC469748
0.7419	Intermediate Similarity	NPC30456
0.7416	Intermediate Similarity	NPC470306
0.7416	Intermediate Similarity	NPC207531
0.7416	Intermediate Similarity	NPC302159
0.7413	Intermediate Similarity	NPC470279
0.7403	Intermediate Similarity	NPC312860
0.74	Intermediate Similarity	NPC320748
0.74	Intermediate Similarity	NPC324245
0.7397	Intermediate Similarity	NPC327904
0.7397	Intermediate Similarity	NPC38959
0.7395	Intermediate Similarity	NPC228377
0.7395	Intermediate Similarity	NPC328186
0.7395	Intermediate Similarity	NPC477787
0.7395	Intermediate Similarity	NPC122968
0.7393	Intermediate Similarity	NPC216428
0.7383	Intermediate Similarity	NPC328154
0.7383	Intermediate Similarity	NPC233727
0.7381	Intermediate Similarity	NPC206343
0.7381	Intermediate Similarity	NPC471014
0.7381	Intermediate Similarity	NPC475408
0.7381	Intermediate Similarity	NPC477908
0.7381	Intermediate Similarity	NPC471016
0.7373	Intermediate Similarity	NPC150698
0.7373	Intermediate Similarity	NPC96801
0.7368	Intermediate Similarity	NPC264674
0.7366	Intermediate Similarity	NPC156044
0.736	Intermediate Similarity	NPC167400
0.7356	Intermediate Similarity	NPC476467
0.7352	Intermediate Similarity	NPC170751
0.7352	Intermediate Similarity	NPC327769
0.735	Intermediate Similarity	NPC90229
0.7346	Intermediate Similarity	NPC319556
0.7346	Intermediate Similarity	NPC187494
0.7343	Intermediate Similarity	NPC123839
0.7333	Intermediate Similarity	NPC194040
0.7333	Intermediate Similarity	NPC62844
0.7333	Intermediate Similarity	NPC193361
0.7321	Intermediate Similarity	NPC317752
0.7317	Intermediate Similarity	NPC309498
0.7316	Intermediate Similarity	NPC139763
0.7315	Intermediate Similarity	NPC124029
0.7313	Intermediate Similarity	NPC59033
0.7313	Intermediate Similarity	NPC317672
0.7311	Intermediate Similarity	NPC472555
0.7311	Intermediate Similarity	NPC84815
0.7311	Intermediate Similarity	NPC301368
0.7308	Intermediate Similarity	NPC251391
0.7306	Intermediate Similarity	NPC238278
0.7302	Intermediate Similarity	NPC477902
0.7299	Intermediate Similarity	NPC6981
0.7294	Intermediate Similarity	NPC316841
0.7293	Intermediate Similarity	NPC313889
0.7292	Intermediate Similarity	NPC164340
0.729	Intermediate Similarity	NPC477788
0.7282	Intermediate Similarity	NPC475835
0.7278	Intermediate Similarity	NPC105811
0.7273	Intermediate Similarity	NPC318299
0.7268	Intermediate Similarity	NPC25442
0.7268	Intermediate Similarity	NPC473239
0.7268	Intermediate Similarity	NPC12944
0.7268	Intermediate Similarity	NPC289086
0.7264	Intermediate Similarity	NPC314270
0.7264	Intermediate Similarity	NPC144779
0.7264	Intermediate Similarity	NPC329024
0.7264	Intermediate Similarity	NPC294579
0.7257	Intermediate Similarity	NPC114310
0.725	Intermediate Similarity	NPC146724
0.7246	Intermediate Similarity	NPC266249
0.7243	Intermediate Similarity	NPC113812
0.7238	Intermediate Similarity	NPC123906
0.7235	Intermediate Similarity	NPC211920
0.7231	Intermediate Similarity	NPC46895
0.723	Intermediate Similarity	NPC74360
0.7217	Intermediate Similarity	NPC326930
0.7217	Intermediate Similarity	NPC475301
0.7215	Intermediate Similarity	NPC477906
0.7209	Intermediate Similarity	NPC127720
0.7209	Intermediate Similarity	NPC127026
0.7208	Intermediate Similarity	NPC278434
0.7207	Intermediate Similarity	NPC230085
0.7207	Intermediate Similarity	NPC159630
0.7204	Intermediate Similarity	NPC4421
0.72	Intermediate Similarity	NPC103230
0.7196	Intermediate Similarity	NPC477901
0.7195	Intermediate Similarity	NPC182222
0.7194	Intermediate Similarity	NPC311282
0.7192	Intermediate Similarity	NPC280714
0.719	Intermediate Similarity	NPC111732
0.719	Intermediate Similarity	NPC323551
0.719	Intermediate Similarity	NPC280473
0.719	Intermediate Similarity	NPC118940
0.719	Intermediate Similarity	NPC292517
0.7188	Intermediate Similarity	NPC84347
0.7176	Intermediate Similarity	NPC471980
0.7167	Intermediate Similarity	NPC467188
0.7167	Intermediate Similarity	NPC473833
0.7163	Intermediate Similarity	NPC477903
0.7157	Intermediate Similarity	NPC118084
0.7156	Intermediate Similarity	NPC51008
0.7156	Intermediate Similarity	NPC41724
0.715	Intermediate Similarity	NPC317373
0.7143	Intermediate Similarity	NPC248782
0.7143	Intermediate Similarity	NPC26881
0.7136	Intermediate Similarity	NPC317572
0.7136	Intermediate Similarity	NPC154339
0.713	Intermediate Similarity	NPC235364
0.7129	Intermediate Similarity	NPC472070
0.7129	Intermediate Similarity	NPC77061
0.7126	Intermediate Similarity	NPC322488
0.7121	Intermediate Similarity	NPC325775
0.7121	Intermediate Similarity	NPC328798
0.7114	Intermediate Similarity	NPC267343
0.7112	Intermediate Similarity	NPC13603
0.7107	Intermediate Similarity	NPC295158
0.7105	Intermediate Similarity	NPC70949
0.7104	Intermediate Similarity	NPC213143
0.7103	Intermediate Similarity	NPC75600
0.7103	Intermediate Similarity	NPC473089
0.7103	Intermediate Similarity	NPC473115

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 NPC109922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	513
0.2-0.3	883
0.3-0.4	1440
0.4-0.5	3125
0.5-0.6	2258
0.6-0.7	708
0.7-0.8	43
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7772	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5088	Discontinued
0.7667	Intermediate Similarity	NPD820	Phase 3
0.765	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD9271	Approved
0.7513	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3947	Discontinued
0.7415	Intermediate Similarity	NPD2509	Approved
0.7415	Intermediate Similarity	NPD2510	Approved
0.7409	Intermediate Similarity	NPD1096	Discontinued
0.7377	Intermediate Similarity	NPD2581	Approved
0.7377	Intermediate Similarity	NPD2582	Approved
0.7374	Intermediate Similarity	NPD4528	Approved
0.7374	Intermediate Similarity	NPD4529	Approved
0.7374	Intermediate Similarity	NPD4526	Approved
0.736	Intermediate Similarity	NPD9074	Approved
0.736	Intermediate Similarity	NPD9075	Approved
0.7321	Intermediate Similarity	NPD3795	Approved
0.7321	Intermediate Similarity	NPD3794	Approved
0.7308	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD8468	Phase 2
0.7232	Intermediate Similarity	NPD107	Approved
0.7225	Intermediate Similarity	NPD5475	Discontinued
0.7216	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5640	Discontinued
0.7184	Intermediate Similarity	NPD6987	Phase 1
0.717	Intermediate Similarity	NPD3394	Approved
0.717	Intermediate Similarity	NPD3389	Approved
0.717	Intermediate Similarity	NPD3393	Approved
0.7165	Intermediate Similarity	NPD1643	Phase 3
0.715	Intermediate Similarity	NPD7010	Phase 3
0.7143	Intermediate Similarity	NPD4417	Approved
0.7129	Intermediate Similarity	NPD6529	Discontinued
0.7128	Intermediate Similarity	NPD3178	Discontinued
0.7101	Intermediate Similarity	NPD7396	Approved
0.71	Intermediate Similarity	NPD2336	Approved
0.7091	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD9510	Approved
0.7056	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3280	Approved
0.7028	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4429	Discontinued
0.7019	Intermediate Similarity	NPD2831	Approved
0.7014	Intermediate Similarity	NPD5022	Discontinued
0.7009	Intermediate Similarity	NPD3006	Discontinued
0.6995	Remote Similarity	NPD1270	Approved
0.6991	Remote Similarity	NPD7404	Approved
0.6991	Remote Similarity	NPD6770	Approved
0.6976	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8356	Approved
0.6968	Remote Similarity	NPD5255	Approved
0.6961	Remote Similarity	NPD2307	Discontinued
0.6961	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD9362	Approved
0.6952	Remote Similarity	NPD3371	Approved
0.695	Remote Similarity	NPD9364	Phase 2
0.695	Remote Similarity	NPD9363	Approved
0.6947	Remote Similarity	NPD1631	Approved
0.6933	Remote Similarity	NPD5891	Approved
0.693	Remote Similarity	NPD1483	Discontinued
0.6927	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2077	Approved
0.6907	Remote Similarity	NPD2076	Approved
0.6901	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5416	Discontinued
0.6897	Remote Similarity	NPD4376	Phase 3
0.6891	Remote Similarity	NPD1573	Approved
0.6891	Remote Similarity	NPD1575	Approved
0.6884	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8063	Discontinued
0.6875	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5866	Approved
0.6869	Remote Similarity	NPD7069	Discontinued
0.6866	Remote Similarity	NPD7395	Discontinued
0.685	Remote Similarity	NPD4889	Approved
0.6847	Remote Similarity	NPD8430	Approved
0.684	Remote Similarity	NPD7467	Discontinued
0.6836	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2896	Discontinued
0.6832	Remote Similarity	NPD7233	Approved
0.6832	Remote Similarity	NPD7234	Approved
0.6831	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8325	Phase 3
0.682	Remote Similarity	NPD8326	Phase 3
0.6813	Remote Similarity	NPD4805	Approved
0.6809	Remote Similarity	NPD2809	Approved
0.6808	Remote Similarity	NPD4506	Discontinued
0.6804	Remote Similarity	NPD1996	Discontinued
0.68	Remote Similarity	NPD721	Approved
0.6798	Remote Similarity	NPD3321	Discontinued
0.6789	Remote Similarity	NPD1630	Approved
0.678	Remote Similarity	NPD1173	Approved
0.6776	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD4301	Approved
0.677	Remote Similarity	NPD4373	Phase 2
0.6768	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4427	Phase 2
0.6745	Remote Similarity	NPD7001	Phase 3
0.6744	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4989	Phase 2
0.6732	Remote Similarity	NPD6569	Phase 2
0.673	Remote Similarity	NPD5513	Phase 2
0.6728	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8479	Phase 2
0.6726	Remote Similarity	NPD8289	Discontinued
0.6717	Remote Similarity	NPD6642	Approved
0.6717	Remote Similarity	NPD6641	Approved
0.6717	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2565	Phase 2
0.6716	Remote Similarity	NPD2564	Approved
0.6715	Remote Similarity	NPD5512	Phase 3
0.6712	Remote Similarity	NPD1623	Approved
0.6711	Remote Similarity	NPD4952	Phase 3
0.6703	Remote Similarity	NPD4804	Approved
0.6698	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5003	Discontinued
0.6682	Remote Similarity	NPD2779	Approved
0.6681	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5482	Discontinued
0.6667	Remote Similarity	NPD7470	Discontinued
0.6667	Remote Similarity	NPD3238	Discontinued
0.6667	Remote Similarity	NPD2511	Approved
0.6652	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7031	Phase 1
0.665	Remote Similarity	NPD2479	Phase 3
0.665	Remote Similarity	NPD6665	Discontinued
0.665	Remote Similarity	NPD2481	Approved
0.6649	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5429	Discontinued
0.6634	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2753	Discontinued
0.6623	Remote Similarity	NPD7885	Phase 2
0.6623	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7886	Phase 2
0.6622	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5901	Discontinued
0.6618	Remote Similarity	NPD4948	Discontinued
0.6609	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3925	Approved
0.66	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6635	Approved
0.6588	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5862	Discovery
0.658	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD272	Approved
0.6574	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3315	Phase 3
0.6565	Remote Similarity	NPD7853	Phase 2
0.6564	Remote Similarity	NPD1659	Phase 1
0.6562	Remote Similarity	NPD9382	Approved
0.6562	Remote Similarity	NPD6173	Approved
0.6562	Remote Similarity	NPD9383	Approved
0.6561	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD3477	Phase 2
0.6555	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD1213	Phase 3
0.6553	Remote Similarity	NPD6281	Approved
0.6552	Remote Similarity	NPD2096	Phase 2
0.6552	Remote Similarity	NPD3569	Discontinued
0.6552	Remote Similarity	NPD2091	Phase 2
0.6549	Remote Similarity	NPD3259	Approved
0.6549	Remote Similarity	NPD4086	Phase 1
0.6545	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4703	Approved
0.6543	Remote Similarity	NPD4702	Approved
0.6542	Remote Similarity	NPD4036	Approved
0.6542	Remote Similarity	NPD4035	Approved
0.6542	Remote Similarity	NPD4033	Approved
0.6542	Remote Similarity	NPD4038	Approved
0.6542	Remote Similarity	NPD31	Approved
0.6542	Remote Similarity	NPD4039	Approved
0.6542	Remote Similarity	NPD944	Approved
0.6542	Remote Similarity	NPD4034	Approved
0.6542	Remote Similarity	NPD4037	Approved
0.6542	Remote Similarity	NPD32	Approved
0.6542	Remote Similarity	NPD4122	Approved
0.654	Remote Similarity	NPD2778	Approved
0.654	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD1229	Phase 2
0.6517	Remote Similarity	NPD1587	Approved
0.6515	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4901	Clinical (unspecified phase)

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