NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.1
Volume:	272.236
LogP:	2.539
LogD:	2.427
LogS:	-3.77
# Rotatable Bonds:	2
TPSA:	63.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	2.669
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.654
MDCK Permeability:	2.3037044229567982e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.44
Plasma Protein Binding (PPB):	92.72525787353516%
Volume Distribution (VD):	0.556
Pgp-substrate:	3.742828845977783%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.752
CYP2C19-substrate:	0.633
CYP2C9-inhibitor:	0.669
CYP2C9-substrate:	0.709
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.67
CYP3A4-inhibitor:	0.339
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	9.186
Half-life (T1/2):	0.612

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.55
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.209
Carcinogencity:	0.777
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.712

Download Data

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

Natural Product: NPC172222

Natural Product ID:	NPC172222
*Common Name:**	Limazepine D
IUPAC Name:	8-ethyl-4-hydroxy-3-methoxypyrrolo[2,1-c][1,4]benzodiazepin-11-one
Synonyms:	Limazepine D
Standard InCHIKey:	SKMAAAVNEKWJHB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14N2O3/c1-3-9-6-10-7-16-13-11(15(19)17(10)8-9)4-5-12(20-2)14(13)18/h4-8,18H,3H2,1-2H3
SMILES:	CCc1cc2cnc3c(ccc(c3O)OC)c(=O)n2c1
Synthetic Gene Cluster:	BGC0001652;
ChEMBL Identifier:	CHEMBL555053
PubChem CID:	42639335
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000295] Benzodiazepines [CHEMONTID:0004097] 1,4-benzodiazepines

*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
NPO32521	micrococcus sp.	Species	Micrococcaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[19388705]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	9.0	mm	PMID[526680]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.0	mm	PMID[526680]

☑ 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 NPC172222 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	705
0.1-0.2	6779
0.2-0.3	10789
0.3-0.4	8165
0.4-0.5	12196
0.5-0.6	2719
0.6-0.7	1181
0.7-0.8	160
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8606	High Similarity	NPC163829
0.8476	Intermediate Similarity	NPC158551
0.7974	Intermediate Similarity	NPC246381
0.7892	Intermediate Similarity	NPC173080
0.7802	Intermediate Similarity	NPC253675
0.7752	Intermediate Similarity	NPC210256
0.7741	Intermediate Similarity	NPC270515
0.7724	Intermediate Similarity	NPC132385
0.7669	Intermediate Similarity	NPC41501
0.7668	Intermediate Similarity	NPC316981
0.7588	Intermediate Similarity	NPC54066
0.7562	Intermediate Similarity	NPC134637
0.7522	Intermediate Similarity	NPC146976
0.7479	Intermediate Similarity	NPC161801
0.7478	Intermediate Similarity	NPC236668
0.7476	Intermediate Similarity	NPC270301
0.7467	Intermediate Similarity	NPC74360
0.7456	Intermediate Similarity	NPC313327
0.7444	Intermediate Similarity	NPC183777
0.7397	Intermediate Similarity	NPC127085
0.7378	Intermediate Similarity	NPC174758
0.7368	Intermediate Similarity	NPC303374
0.7366	Intermediate Similarity	NPC193238
0.7355	Intermediate Similarity	NPC15406
0.7339	Intermediate Similarity	NPC122436
0.7325	Intermediate Similarity	NPC162530
0.7325	Intermediate Similarity	NPC266931
0.7319	Intermediate Similarity	NPC74575
0.7308	Intermediate Similarity	NPC179287
0.7304	Intermediate Similarity	NPC473513
0.7296	Intermediate Similarity	NPC210434
0.7295	Intermediate Similarity	NPC107123
0.7288	Intermediate Similarity	NPC66777
0.7284	Intermediate Similarity	NPC160100
0.7281	Intermediate Similarity	NPC202605
0.7281	Intermediate Similarity	NPC219087
0.7281	Intermediate Similarity	NPC112206
0.7273	Intermediate Similarity	NPC210296
0.7257	Intermediate Similarity	NPC171787
0.7254	Intermediate Similarity	NPC208522
0.725	Intermediate Similarity	NPC477549
0.7247	Intermediate Similarity	NPC77878
0.7244	Intermediate Similarity	NPC472286
0.7244	Intermediate Similarity	NPC472287
0.7238	Intermediate Similarity	NPC22481
0.7227	Intermediate Similarity	NPC260434
0.7225	Intermediate Similarity	NPC174672
0.7215	Intermediate Similarity	NPC471762
0.7205	Intermediate Similarity	NPC470481
0.7205	Intermediate Similarity	NPC470482
0.7197	Intermediate Similarity	NPC49547
0.7188	Intermediate Similarity	NPC295898
0.7188	Intermediate Similarity	NPC135887
0.7188	Intermediate Similarity	NPC199277
0.7186	Intermediate Similarity	NPC274982
0.7185	Intermediate Similarity	NPC278525
0.7185	Intermediate Similarity	NPC24019
0.7182	Intermediate Similarity	NPC326634
0.7181	Intermediate Similarity	NPC82548
0.7181	Intermediate Similarity	NPC18348
0.7177	Intermediate Similarity	NPC183537
0.7173	Intermediate Similarity	NPC257851
0.7167	Intermediate Similarity	NPC17565
0.7166	Intermediate Similarity	NPC91868
0.7166	Intermediate Similarity	NPC63971
0.7162	Intermediate Similarity	NPC146418
0.7156	Intermediate Similarity	NPC53144
0.7149	Intermediate Similarity	NPC189903
0.7149	Intermediate Similarity	NPC182907
0.7143	Intermediate Similarity	NPC194740
0.7143	Intermediate Similarity	NPC316224
0.7131	Intermediate Similarity	NPC470018
0.713	Intermediate Similarity	NPC295158
0.7124	Intermediate Similarity	NPC182853
0.7118	Intermediate Similarity	NPC470020
0.7118	Intermediate Similarity	NPC309845
0.7117	Intermediate Similarity	NPC90229
0.7107	Intermediate Similarity	NPC108342
0.7106	Intermediate Similarity	NPC60621
0.708	Intermediate Similarity	NPC475774
0.7078	Intermediate Similarity	NPC473183
0.7078	Intermediate Similarity	NPC470022
0.7078	Intermediate Similarity	NPC472061
0.7078	Intermediate Similarity	NPC235685
0.7076	Intermediate Similarity	NPC220851
0.7066	Intermediate Similarity	NPC182222
0.7061	Intermediate Similarity	NPC119134
0.7061	Intermediate Similarity	NPC148889
0.7061	Intermediate Similarity	NPC16249
0.7051	Intermediate Similarity	NPC303658
0.7049	Intermediate Similarity	NPC101350
0.7046	Intermediate Similarity	NPC65277
0.704	Intermediate Similarity	NPC473188
0.7031	Intermediate Similarity	NPC287208
0.7029	Intermediate Similarity	NPC157931
0.7022	Intermediate Similarity	NPC234197
0.7022	Intermediate Similarity	NPC477019
0.7021	Intermediate Similarity	NPC208084
0.702	Intermediate Similarity	NPC282346
0.7018	Intermediate Similarity	NPC315499
0.7017	Intermediate Similarity	NPC97746
0.7016	Intermediate Similarity	NPC58209
0.7013	Intermediate Similarity	NPC87413
0.7012	Intermediate Similarity	NPC217176
0.7009	Intermediate Similarity	NPC472284
0.7004	Intermediate Similarity	NPC200836
0.7004	Intermediate Similarity	NPC188400
0.7	Intermediate Similarity	NPC325297
0.6996	Remote Similarity	NPC2905
0.6996	Remote Similarity	NPC34770
0.6996	Remote Similarity	NPC90875
0.6996	Remote Similarity	NPC473184
0.6992	Remote Similarity	NPC128115
0.6992	Remote Similarity	NPC276657
0.6987	Remote Similarity	NPC321428
0.6983	Remote Similarity	NPC264176
0.6983	Remote Similarity	NPC233334
0.6983	Remote Similarity	NPC196718
0.6983	Remote Similarity	NPC102593
0.698	Remote Similarity	NPC166722
0.698	Remote Similarity	NPC474183
0.6979	Remote Similarity	NPC264285
0.6979	Remote Similarity	NPC134702
0.6979	Remote Similarity	NPC473822
0.6976	Remote Similarity	NPC78609
0.6976	Remote Similarity	NPC124313
0.6975	Remote Similarity	NPC205372
0.6974	Remote Similarity	NPC476581
0.6974	Remote Similarity	NPC36229
0.6974	Remote Similarity	NPC16452
0.6972	Remote Similarity	NPC241025
0.697	Remote Similarity	NPC85273
0.6969	Remote Similarity	NPC258048
0.6964	Remote Similarity	NPC207283
0.6964	Remote Similarity	NPC84164
0.696	Remote Similarity	NPC211813
0.6957	Remote Similarity	NPC207873
0.6957	Remote Similarity	NPC100573
0.6955	Remote Similarity	NPC329631
0.6941	Remote Similarity	NPC216369
0.694	Remote Similarity	NPC295479
0.694	Remote Similarity	NPC220241
0.6937	Remote Similarity	NPC195268
0.6937	Remote Similarity	NPC133140
0.6933	Remote Similarity	NPC118121
0.6926	Remote Similarity	NPC469589
0.6926	Remote Similarity	NPC208898
0.6923	Remote Similarity	NPC99891
0.692	Remote Similarity	NPC251090
0.6913	Remote Similarity	NPC53344
0.691	Remote Similarity	NPC296482
0.691	Remote Similarity	NPC202768
0.691	Remote Similarity	NPC53069
0.6909	Remote Similarity	NPC46580
0.6907	Remote Similarity	NPC204446
0.6907	Remote Similarity	NPC184408
0.6907	Remote Similarity	NPC247803
0.6906	Remote Similarity	NPC307963
0.6906	Remote Similarity	NPC230403
0.6905	Remote Similarity	NPC137353
0.6904	Remote Similarity	NPC94842
0.6904	Remote Similarity	NPC322482
0.6903	Remote Similarity	NPC476578
0.6903	Remote Similarity	NPC476582
0.6903	Remote Similarity	NPC4071
0.69	Remote Similarity	NPC472259
0.6898	Remote Similarity	NPC470017
0.6895	Remote Similarity	NPC72905
0.6895	Remote Similarity	NPC282103
0.6894	Remote Similarity	NPC470799
0.6894	Remote Similarity	NPC8022
0.6892	Remote Similarity	NPC92803
0.6891	Remote Similarity	NPC118189
0.6891	Remote Similarity	NPC76478
0.6888	Remote Similarity	NPC478078
0.6883	Remote Similarity	NPC39679
0.688	Remote Similarity	NPC232225
0.688	Remote Similarity	NPC114468
0.6878	Remote Similarity	NPC18890
0.6875	Remote Similarity	NPC93390
0.6873	Remote Similarity	NPC207620
0.687	Remote Similarity	NPC184680
0.6866	Remote Similarity	NPC98416
0.686	Remote Similarity	NPC209981
0.6851	Remote Similarity	NPC118228
0.6851	Remote Similarity	NPC148391
0.6849	Remote Similarity	NPC150239
0.6848	Remote Similarity	NPC169716
0.6846	Remote Similarity	NPC24370
0.6846	Remote Similarity	NPC319232
0.6842	Remote Similarity	NPC31930
0.6842	Remote Similarity	NPC470784
0.6842	Remote Similarity	NPC470785
0.684	Remote Similarity	NPC4687
0.684	Remote Similarity	NPC249583
0.684	Remote Similarity	NPC313189
0.6838	Remote Similarity	NPC96405
0.6838	Remote Similarity	NPC171409
0.6833	Remote Similarity	NPC314633
0.6832	Remote Similarity	NPC101312

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 NPC172222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	773
0.2-0.3	1040
0.3-0.4	2037
0.4-0.5	2678
0.5-0.6	1678
0.6-0.7	553
0.7-0.8	23
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
0.7884	Intermediate Similarity	NPD8091	Phase 3
0.7541	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7559	Phase 2
0.7417	Intermediate Similarity	NPD6790	Phase 1
0.7384	Intermediate Similarity	NPD4373	Phase 2
0.7277	Intermediate Similarity	NPD5640	Discontinued
0.7257	Intermediate Similarity	NPD5022	Discontinued
0.7257	Intermediate Similarity	NPD4952	Phase 3
0.7243	Intermediate Similarity	NPD6716	Phase 1
0.7215	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4429	Discontinued
0.7185	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD3259	Approved
0.7172	Intermediate Similarity	NPD1483	Discontinued
0.7156	Intermediate Similarity	NPD5513	Phase 2
0.7155	Intermediate Similarity	NPD1505	Phase 2
0.7155	Intermediate Similarity	NPD6962	Phase 2
0.7137	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3006	Discontinued
0.7102	Intermediate Similarity	NPD6517	Phase 3
0.7101	Intermediate Similarity	NPD4845	Discontinued
0.709	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6963	Approved
0.7066	Intermediate Similarity	NPD6964	Approved
0.7064	Intermediate Similarity	NPD6242	Discontinued
0.7059	Intermediate Similarity	NPD7426	Phase 1
0.7056	Intermediate Similarity	NPD5866	Approved
0.7031	Intermediate Similarity	NPD7467	Discontinued
0.702	Intermediate Similarity	NPD7886	Phase 2
0.702	Intermediate Similarity	NPD7885	Phase 2
0.7013	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD4049	Phase 2
0.6987	Remote Similarity	NPD1392	Approved
0.6983	Remote Similarity	NPD7031	Phase 1
0.6974	Remote Similarity	NPD3947	Discontinued
0.696	Remote Similarity	NPD956	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7013	Phase 3
0.696	Remote Similarity	NPD7012	Phase 3
0.6955	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3921	Approved
0.6937	Remote Similarity	NPD3924	Approved
0.6937	Remote Similarity	NPD3923	Approved
0.6937	Remote Similarity	NPD3922	Approved
0.6932	Remote Similarity	NPD7588	Discontinued
0.692	Remote Similarity	NPD8479	Phase 2
0.6914	Remote Similarity	NPD6228	Discontinued
0.691	Remote Similarity	NPD3815	Phase 1
0.691	Remote Similarity	NPD3816	Phase 1
0.6907	Remote Similarity	NPD5632	Approved
0.6906	Remote Similarity	NPD1038	Approved
0.6897	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5612	Discontinued
0.6883	Remote Similarity	NPD5658	Approved
0.6878	Remote Similarity	NPD3258	Approved
0.6877	Remote Similarity	NPD7859	Phase 2
0.687	Remote Similarity	NPD5601	Phase 2
0.6867	Remote Similarity	NPD683	Approved
0.6862	Remote Similarity	NPD1954	Phase 1
0.6862	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2951	Discontinued
0.6851	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5293	Phase 2
0.684	Remote Similarity	NPD7453	Approved
0.684	Remote Similarity	NPD7452	Approved
0.6837	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7924	Phase 2
0.682	Remote Similarity	NPD7925	Phase 2
0.6818	Remote Similarity	NPD4328	Approved
0.6816	Remote Similarity	NPD6494	Phase 2
0.6816	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8016	Phase 3
0.6812	Remote Similarity	NPD824	Approved
0.6807	Remote Similarity	NPD2899	Discontinued
0.6798	Remote Similarity	NPD484	Approved
0.6793	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3257	Approved
0.6778	Remote Similarity	NPD7180	Phase 3
0.6777	Remote Similarity	NPD7603	Discontinued
0.6776	Remote Similarity	NPD4885	Approved
0.6774	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7222	Phase 2
0.6765	Remote Similarity	NPD3354	Phase 2
0.6761	Remote Similarity	NPD7853	Phase 2
0.6761	Remote Similarity	NPD5469	Phase 3
0.6759	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4558	Phase 2
0.6749	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4368	Phase 2
0.6724	Remote Similarity	NPD3507	Phase 2
0.6723	Remote Similarity	NPD4131	Phase 3
0.672	Remote Similarity	NPD7417	Discontinued
0.6719	Remote Similarity	NPD8463	Approved
0.6709	Remote Similarity	NPD4897	Phase 2
0.6695	Remote Similarity	NPD3313	Phase 2
0.6695	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7225	Discontinued
0.6694	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4369	Phase 2
0.6681	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD1768	Approved
0.6681	Remote Similarity	NPD5025	Approved
0.668	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD7803	Approved
0.6667	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3763	Approved
0.6667	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD4989	Phase 2
0.6652	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD1740	Approved
0.6652	Remote Similarity	NPD1739	Approved
0.6652	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4418	Discontinued
0.6651	Remote Similarity	NPD2821	Approved
0.6642	Remote Similarity	NPD3217	Phase 2
0.664	Remote Similarity	NPD6727	Phase 2
0.664	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4372	Phase 1
0.6627	Remote Similarity	NPD7022	Phase 2
0.6627	Remote Similarity	NPD3322	Phase 1
0.6627	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD1659	Phase 1
0.6626	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD6568	Discontinued
0.6624	Remote Similarity	NPD7069	Discontinued
0.6622	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7558	Phase 2
0.6613	Remote Similarity	NPD4080	Discontinued
0.661	Remote Similarity	NPD5914	Approved
0.6609	Remote Similarity	NPD4795	Phase 2
0.6608	Remote Similarity	NPD4551	Phase 2
0.6606	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5482	Discontinued
0.6602	Remote Similarity	NPD3809	Discontinued
0.6595	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD1622	Discontinued
0.6592	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.659	Remote Similarity	NPD5116	Phase 1
0.659	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD2757	Phase 2
0.6584	Remote Similarity	NPD6209	Approved
0.6584	Remote Similarity	NPD8356	Approved
0.6583	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5416	Discontinued
0.6581	Remote Similarity	NPD7001	Phase 3
0.658	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD2792	Approved
0.6578	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7797	Approved
0.6573	Remote Similarity	NPD7796	Approved
0.6571	Remote Similarity	NPD3263	Phase 3
0.6571	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5903	Approved
0.6569	Remote Similarity	NPD5902	Approved
0.6569	Remote Similarity	NPD5149	Phase 2
0.6569	Remote Similarity	NPD1955	Discontinued
0.6569	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5071	Phase 2
0.6565	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD9510	Approved
0.6547	Remote Similarity	NPD1096	Discontinued
0.6545	Remote Similarity	NPD8430	Approved
0.6543	Remote Similarity	NPD5506	Approved
0.6543	Remote Similarity	NPD4923	Phase 1
0.6543	Remote Similarity	NPD5507	Approved
0.6542	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.654	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD32	Approved
0.6538	Remote Similarity	NPD4122	Approved
0.6538	Remote Similarity	NPD6961	Discontinued
0.6538	Remote Similarity	NPD31	Approved
0.6538	Remote Similarity	NPD4034	Approved
0.6538	Remote Similarity	NPD4033	Approved
0.6538	Remote Similarity	NPD4035	Approved
0.6538	Remote Similarity	NPD4038	Approved
0.6538	Remote Similarity	NPD4039	Approved
0.6538	Remote Similarity	NPD4037	Approved
0.6538	Remote Similarity	NPD4036	Approved
0.6533	Remote Similarity	NPD4948	Discontinued
0.6533	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5519	Discontinued
0.6527	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7708	Approved
0.6527	Remote Similarity	NPD3945	Discontinued
0.6525	Remote Similarity	NPD2510	Approved
0.6525	Remote Similarity	NPD2916	Discontinued
0.6525	Remote Similarity	NPD2509	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