NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	229.07
Volume:	229.284
LogP:	2.176
LogD:	2.63
LogS:	-3.266
# Rotatable Bonds:	1
TPSA:	44.37
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	2.505
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822
MDCK Permeability:	3.4987842809641734e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.164

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.865
Plasma Protein Binding (PPB):	88.34001922607422%
Volume Distribution (VD):	0.684
Pgp-substrate:	8.284195899963379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.648
CYP2C9-inhibitor:	0.526
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.718
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	8.574
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.604
AMES Toxicity:	0.916
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.617
Skin Sensitization:	0.097
Carcinogencity:	0.949
Eye Corrosion:	0.006
Eye Irritation:	0.774
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC146418

Natural Product ID:	NPC146418
*Common Name:**	Koniamborine
IUPAC Name:	7-methoxy-5-methylpyrano[3,2-b]indol-4-one
Synonyms:	Koniamborine
Standard InCHIKey:	MHWZBYSZMPRYHU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11NO3/c1-14-10-7-8(16-2)3-4-9(10)13-12(14)11(15)5-6-17-13/h3-7H,1-2H3
SMILES:	Cn1c2cc(ccc2c2c1c(=O)cco2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486605
PubChem CID:	11345225
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004197] N-alkylindoles

*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
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038554]
NPO6978	Boronella koniambiensis	Species	Rutaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	38200.0	nM	PMID[506651]

☑ 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 NPC146418 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	633
0.1-0.2	4259
0.2-0.3	12679
0.3-0.4	5433
0.4-0.5	12948
0.5-0.6	5026
0.6-0.7	1391
0.7-0.8	308
0.8-0.85	18
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8143	Intermediate Similarity	NPC208084
0.8116	Intermediate Similarity	NPC308137
0.8116	Intermediate Similarity	NPC310211
0.8057	Intermediate Similarity	NPC298436
0.8049	Intermediate Similarity	NPC249583
0.8029	Intermediate Similarity	NPC264176
0.8009	Intermediate Similarity	NPC194740
0.8	Intermediate Similarity	NPC472287
0.8	Intermediate Similarity	NPC472286
0.7961	Intermediate Similarity	NPC4687
0.7952	Intermediate Similarity	NPC116238
0.7941	Intermediate Similarity	NPC295898
0.7925	Intermediate Similarity	NPC46561
0.7925	Intermediate Similarity	NPC247803
0.7908	Intermediate Similarity	NPC241025
0.7897	Intermediate Similarity	NPC198503
0.7877	Intermediate Similarity	NPC169402
0.7874	Intermediate Similarity	NPC321428
0.787	Intermediate Similarity	NPC179287
0.787	Intermediate Similarity	NPC97746
0.785	Intermediate Similarity	NPC150239
0.781	Intermediate Similarity	NPC187501
0.781	Intermediate Similarity	NPC87413
0.7773	Intermediate Similarity	NPC260434
0.7767	Intermediate Similarity	NPC174760
0.7748	Intermediate Similarity	NPC34770
0.7745	Intermediate Similarity	NPC472284
0.7742	Intermediate Similarity	NPC122436
0.7736	Intermediate Similarity	NPC39500
0.7706	Intermediate Similarity	NPC21638
0.7685	Intermediate Similarity	NPC225279
0.7678	Intermediate Similarity	NPC269367
0.7674	Intermediate Similarity	NPC303658
0.7674	Intermediate Similarity	NPC131885
0.7636	Intermediate Similarity	NPC140296
0.7635	Intermediate Similarity	NPC230403
0.7615	Intermediate Similarity	NPC144452
0.7613	Intermediate Similarity	NPC217176
0.76	Intermediate Similarity	NPC472061
0.7593	Intermediate Similarity	NPC184408
0.7589	Intermediate Similarity	NPC39370
0.7583	Intermediate Similarity	NPC39679
0.7581	Intermediate Similarity	NPC3207
0.7578	Intermediate Similarity	NPC473186
0.7571	Intermediate Similarity	NPC45190
0.7547	Intermediate Similarity	NPC174758
0.7546	Intermediate Similarity	NPC305984
0.7544	Intermediate Similarity	NPC166712
0.7535	Intermediate Similarity	NPC16066
0.7523	Intermediate Similarity	NPC54066
0.7511	Intermediate Similarity	NPC208364
0.7511	Intermediate Similarity	NPC160100
0.75	Intermediate Similarity	NPC84478
0.75	Intermediate Similarity	NPC62069
0.75	Intermediate Similarity	NPC287208
0.75	Intermediate Similarity	NPC148183
0.75	Intermediate Similarity	NPC86834
0.75	Intermediate Similarity	NPC152768
0.75	Intermediate Similarity	NPC210828
0.7489	Intermediate Similarity	NPC474183
0.7488	Intermediate Similarity	NPC300156
0.7477	Intermediate Similarity	NPC23294
0.7477	Intermediate Similarity	NPC288987
0.7467	Intermediate Similarity	NPC329631
0.7455	Intermediate Similarity	NPC474688
0.7446	Intermediate Similarity	NPC58209
0.7445	Intermediate Similarity	NPC6786
0.7445	Intermediate Similarity	NPC235685
0.7445	Intermediate Similarity	NPC184680
0.7444	Intermediate Similarity	NPC274640
0.7444	Intermediate Similarity	NPC471762
0.743	Intermediate Similarity	NPC303951
0.7424	Intermediate Similarity	NPC148889
0.7421	Intermediate Similarity	NPC205372
0.7412	Intermediate Similarity	NPC101350
0.7412	Intermediate Similarity	NPC470785
0.7384	Intermediate Similarity	NPC258048
0.7383	Intermediate Similarity	NPC174672
0.7382	Intermediate Similarity	NPC173250
0.738	Intermediate Similarity	NPC168922
0.7376	Intermediate Similarity	NPC295158
0.7366	Intermediate Similarity	NPC66777
0.7364	Intermediate Similarity	NPC472099
0.7364	Intermediate Similarity	NPC323969
0.7361	Intermediate Similarity	NPC472098
0.7354	Intermediate Similarity	NPC470018
0.7352	Intermediate Similarity	NPC473041
0.735	Intermediate Similarity	NPC203373
0.735	Intermediate Similarity	NPC165964
0.7349	Intermediate Similarity	NPC470020
0.7342	Intermediate Similarity	NPC53534
0.7339	Intermediate Similarity	NPC274982
0.7336	Intermediate Similarity	NPC470784
0.7321	Intermediate Similarity	NPC306376
0.732	Intermediate Similarity	NPC118511
0.7308	Intermediate Similarity	NPC91868
0.7308	Intermediate Similarity	NPC63971
0.7303	Intermediate Similarity	NPC152620
0.7302	Intermediate Similarity	NPC325297
0.7302	Intermediate Similarity	NPC469589
0.7297	Intermediate Similarity	NPC216612
0.7294	Intermediate Similarity	NPC118228
0.729	Intermediate Similarity	NPC193238
0.7284	Intermediate Similarity	NPC188400
0.7277	Intermediate Similarity	NPC132539
0.7273	Intermediate Similarity	NPC174576
0.7269	Intermediate Similarity	NPC196718
0.7269	Intermediate Similarity	NPC102593
0.7265	Intermediate Similarity	NPC314633
0.7252	Intermediate Similarity	NPC60621
0.7248	Intermediate Similarity	NPC236668
0.7244	Intermediate Similarity	NPC478078
0.7237	Intermediate Similarity	NPC473105
0.7235	Intermediate Similarity	NPC220337
0.7233	Intermediate Similarity	NPC144381
0.723	Intermediate Similarity	NPC317572
0.723	Intermediate Similarity	NPC134848
0.7229	Intermediate Similarity	NPC41501
0.7225	Intermediate Similarity	NPC26872
0.7215	Intermediate Similarity	NPC146976
0.7207	Intermediate Similarity	NPC128115
0.7206	Intermediate Similarity	NPC42591
0.7205	Intermediate Similarity	NPC182222
0.7204	Intermediate Similarity	NPC220408
0.7202	Intermediate Similarity	NPC118940
0.7198	Intermediate Similarity	NPC475844
0.7197	Intermediate Similarity	NPC120513
0.7194	Intermediate Similarity	NPC299582
0.7191	Intermediate Similarity	NPC1608
0.719	Intermediate Similarity	NPC267928
0.7188	Intermediate Similarity	NPC322482
0.7188	Intermediate Similarity	NPC51388
0.7186	Intermediate Similarity	NPC166722
0.7174	Intermediate Similarity	NPC473187
0.7173	Intermediate Similarity	NPC67401
0.7171	Intermediate Similarity	NPC194040
0.7168	Intermediate Similarity	NPC74575
0.7162	Intermediate Similarity	NPC172222
0.715	Intermediate Similarity	NPC475774
0.7143	Intermediate Similarity	NPC477587
0.7143	Intermediate Similarity	NPC477589
0.713	Intermediate Similarity	NPC283117
0.713	Intermediate Similarity	NPC53344
0.713	Intermediate Similarity	NPC183777
0.713	Intermediate Similarity	NPC253675
0.7125	Intermediate Similarity	NPC318068
0.7124	Intermediate Similarity	NPC119134
0.7123	Intermediate Similarity	NPC280714
0.7123	Intermediate Similarity	NPC474428
0.7118	Intermediate Similarity	NPC49547
0.7116	Intermediate Similarity	NPC470930
0.7115	Intermediate Similarity	NPC1820
0.7114	Intermediate Similarity	NPC286195
0.7113	Intermediate Similarity	NPC26850
0.7111	Intermediate Similarity	NPC94842
0.7105	Intermediate Similarity	NPC24019
0.7103	Intermediate Similarity	NPC57398
0.7103	Intermediate Similarity	NPC66815
0.7101	Intermediate Similarity	NPC242928
0.71	Intermediate Similarity	NPC470017
0.71	Intermediate Similarity	NPC108342
0.7098	Intermediate Similarity	NPC280799
0.7097	Intermediate Similarity	NPC82548
0.7095	Intermediate Similarity	NPC131017
0.7091	Intermediate Similarity	NPC89508
0.7089	Intermediate Similarity	NPC329747
0.7087	Intermediate Similarity	NPC160381
0.7082	Intermediate Similarity	NPC477586
0.7082	Intermediate Similarity	NPC477588
0.7082	Intermediate Similarity	NPC477590
0.7082	Intermediate Similarity	NPC477585
0.7081	Intermediate Similarity	NPC114039
0.7081	Intermediate Similarity	NPC206109
0.7078	Intermediate Similarity	NPC294375
0.7078	Intermediate Similarity	NPC282346
0.7075	Intermediate Similarity	NPC72211
0.7074	Intermediate Similarity	NPC474701
0.7073	Intermediate Similarity	NPC258480
0.7072	Intermediate Similarity	NPC293151
0.7069	Intermediate Similarity	NPC182907
0.7069	Intermediate Similarity	NPC189903
0.7067	Intermediate Similarity	NPC210434
0.7066	Intermediate Similarity	NPC129897
0.7064	Intermediate Similarity	NPC185782
0.7061	Intermediate Similarity	NPC88923
0.7061	Intermediate Similarity	NPC315634
0.7061	Intermediate Similarity	NPC100734
0.7059	Intermediate Similarity	NPC474798
0.7056	Intermediate Similarity	NPC470586
0.7056	Intermediate Similarity	NPC232727
0.7049	Intermediate Similarity	NPC230683
0.7045	Intermediate Similarity	NPC26679
0.7042	Intermediate Similarity	NPC123395
0.7042	Intermediate Similarity	NPC128823
0.704	Intermediate Similarity	NPC469594
0.7037	Intermediate Similarity	NPC185197
0.7037	Intermediate Similarity	NPC285558
0.7037	Intermediate Similarity	NPC89549
0.7035	Intermediate Similarity	NPC470894
0.7032	Intermediate Similarity	NPC471304

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 NPC146418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	709
0.2-0.3	1014
0.3-0.4	1701
0.4-0.5	2905
0.5-0.6	1793
0.6-0.7	592
0.7-0.8	73
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
0.7963	Intermediate Similarity	NPD3259	Approved
0.7812	Intermediate Similarity	NPD6790	Phase 1
0.7757	Intermediate Similarity	NPD5632	Approved
0.7746	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1505	Phase 2
0.7678	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4952	Phase 3
0.7639	Intermediate Similarity	NPD6974	Phase 3
0.7611	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD5866	Approved
0.7604	Intermediate Similarity	NPD7180	Phase 3
0.7576	Intermediate Similarity	NPD5482	Discontinued
0.7559	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4373	Phase 2
0.75	Intermediate Similarity	NPD7031	Phase 1
0.75	Intermediate Similarity	NPD7417	Discontinued
0.7488	Intermediate Similarity	NPD3945	Discontinued
0.7477	Intermediate Similarity	NPD7994	Phase 2
0.7467	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1867	Approved
0.7455	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2778	Approved
0.743	Intermediate Similarity	NPD3392	Approved
0.7421	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5924	Discontinued
0.7401	Intermediate Similarity	NPD7853	Phase 2
0.7391	Intermediate Similarity	NPD6716	Phase 1
0.7387	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6962	Phase 2
0.7373	Intermediate Similarity	NPD3257	Approved
0.7352	Intermediate Similarity	NPD4429	Discontinued
0.7346	Intermediate Similarity	NPD2779	Approved
0.7343	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5479	Discontinued
0.7321	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5512	Phase 3
0.7294	Intermediate Similarity	NPD5293	Phase 2
0.7293	Intermediate Similarity	NPD4368	Phase 2
0.7285	Intermediate Similarity	NPD6242	Discontinued
0.726	Intermediate Similarity	NPD4418	Discontinued
0.7257	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3006	Discontinued
0.724	Intermediate Similarity	NPD3258	Approved
0.723	Intermediate Similarity	NPD5513	Phase 2
0.722	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5450	Discontinued
0.7181	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1630	Approved
0.7143	Intermediate Similarity	NPD6550	Discontinued
0.7136	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7453	Approved
0.713	Intermediate Similarity	NPD7222	Phase 2
0.713	Intermediate Similarity	NPD7452	Approved
0.7124	Intermediate Similarity	NPD3263	Phase 3
0.7123	Intermediate Similarity	NPD1768	Approved
0.7113	Intermediate Similarity	NPD6252	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5532	Phase 2
0.7105	Intermediate Similarity	NPD5022	Discontinued
0.7093	Intermediate Similarity	NPD4328	Approved
0.7078	Intermediate Similarity	NPD5416	Discontinued
0.7075	Intermediate Similarity	NPD772	Phase 3
0.7074	Intermediate Similarity	NPD1467	Approved
0.7074	Intermediate Similarity	NPD1466	Phase 3
0.7072	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD946	Discontinued
0.7069	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7803	Approved
0.7059	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2951	Discontinued
0.7056	Intermediate Similarity	NPD1631	Approved
0.7054	Intermediate Similarity	NPD5850	Phase 3
0.704	Intermediate Similarity	NPD7395	Discontinued
0.7039	Intermediate Similarity	NPD4394	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1659	Phase 1
0.7021	Intermediate Similarity	NPD4322	Discontinued
0.7005	Intermediate Similarity	NPD3003	Approved
0.7	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7955	Approved
0.6996	Remote Similarity	NPD7956	Approved
0.6995	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1638	Discovery
0.6974	Remote Similarity	NPD5640	Discontinued
0.6972	Remote Similarity	NPD1392	Approved
0.6972	Remote Similarity	NPD5429	Discontinued
0.6971	Remote Similarity	NPD8463	Approved
0.6959	Remote Similarity	NPD3947	Discontinued
0.6955	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5658	Approved
0.6933	Remote Similarity	NPD5488	Discontinued
0.693	Remote Similarity	NPD3925	Approved
0.692	Remote Similarity	NPD5922	Phase 3
0.69	Remote Similarity	NPD7426	Phase 1
0.6898	Remote Similarity	NPD7708	Approved
0.6875	Remote Similarity	NPD4558	Phase 2
0.6864	Remote Similarity	NPD7467	Discontinued
0.6862	Remote Similarity	NPD8359	Phase 2
0.6853	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4501	Approved
0.6852	Remote Similarity	NPD4500	Approved
0.6849	Remote Similarity	NPD3507	Phase 2
0.6844	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD8255	Phase 2
0.6842	Remote Similarity	NPD5256	Discontinued
0.6835	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1575	Approved
0.6832	Remote Similarity	NPD1573	Approved
0.6831	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5902	Approved
0.683	Remote Similarity	NPD5903	Approved
0.6828	Remote Similarity	NPD8479	Phase 2
0.6827	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4885	Approved
0.6814	Remote Similarity	NPD1586	Approved
0.6812	Remote Similarity	NPD4203	Approved
0.6812	Remote Similarity	NPD4204	Approved
0.681	Remote Similarity	NPD1034	Phase 3
0.681	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3250	Phase 1
0.6808	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8102	Discontinued
0.6804	Remote Similarity	NPD3397	Phase 2
0.6798	Remote Similarity	NPD4923	Phase 1
0.6791	Remote Similarity	NPD5003	Discontinued
0.6784	Remote Similarity	NPD3875	Discontinued
0.6784	Remote Similarity	NPD6770	Approved
0.6781	Remote Similarity	NPD7688	Phase 1
0.6777	Remote Similarity	NPD2792	Approved
0.6773	Remote Similarity	NPD7001	Phase 3
0.6771	Remote Similarity	NPD4502	Phase 2
0.6762	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6228	Discontinued
0.6745	Remote Similarity	NPD2565	Phase 2
0.6745	Remote Similarity	NPD2564	Approved
0.6744	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3477	Phase 2
0.674	Remote Similarity	NPD6985	Discontinued
0.674	Remote Similarity	NPD3354	Phase 2
0.6736	Remote Similarity	NPD7022	Phase 2
0.6736	Remote Similarity	NPD4369	Phase 2
0.6736	Remote Similarity	NPD6517	Phase 3
0.6729	Remote Similarity	NPD1038	Approved
0.6726	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7886	Phase 2
0.6723	Remote Similarity	NPD4858	Phase 2
0.6723	Remote Similarity	NPD7885	Phase 2
0.6715	Remote Similarity	NPD1587	Approved
0.6714	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6988	Phase 1
0.6712	Remote Similarity	NPD2916	Discontinued
0.6711	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2884	Phase 1
0.6709	Remote Similarity	NPD5805	Approved
0.6708	Remote Similarity	NPD3986	Discontinued
0.6698	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6590	Discontinued
0.6698	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD1739	Approved
0.6697	Remote Similarity	NPD1740	Approved
0.6696	Remote Similarity	NPD6209	Approved
0.6694	Remote Similarity	NPD3328	Phase 2
0.6682	Remote Similarity	NPD4506	Discontinued
0.6682	Remote Similarity	NPD9243	Approved
0.6682	Remote Similarity	NPD6569	Phase 2
0.6681	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7069	Discontinued
0.6667	Remote Similarity	NPD1483	Discontinued
0.6667	Remote Similarity	NPD6568	Discontinued
0.6667	Remote Similarity	NPD6321	Discontinued
0.6667	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7924	Phase 2
0.6667	Remote Similarity	NPD7925	Phase 2
0.6653	Remote Similarity	NPD1927	Discontinued
0.6653	Remote Similarity	NPD7859	Phase 2
0.6653	Remote Similarity	NPD5817	Discontinued
0.6653	Remote Similarity	NPD7558	Phase 2
0.6652	Remote Similarity	NPD4039	Approved
0.6652	Remote Similarity	NPD32	Approved
0.6652	Remote Similarity	NPD4033	Approved
0.6652	Remote Similarity	NPD4034	Approved
0.6652	Remote Similarity	NPD4036	Approved
0.6652	Remote Similarity	NPD31	Approved
0.6652	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4122	Approved
0.6652	Remote Similarity	NPD4795	Phase 2
0.6652	Remote Similarity	NPD4038	Approved
0.6652	Remote Similarity	NPD4035	Approved
0.6652	Remote Similarity	NPD4037	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