NPASS Compound

Structure

NPC470784 OpenBabel07101719512D 31 35 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2545 -0.8136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0898 -2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6667 -1.6226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 31 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 24 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 21 1 0 0 0 0 11 31 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 23 1 0 0 0 0 14 5 1 1 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 6 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 19 27 2 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 20 28 2 0 0 0 0 21 29 1 0 0 0 0 22 25 1 0 0 0 0 22 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	429.19
Volume:	416.199
LogP:	1.382
LogD:	1.435
LogS:	-2.68
# Rotatable Bonds:	3
TPSA:	126.33
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	4.364
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.237
MDCK Permeability:	7.635982910869643e-06
Pgp-inhibitor:	0.031
Pgp-substrate:	0.495
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	47.828765869140625%
Volume Distribution (VD):	1.053
Pgp-substrate:	44.32575988769531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.795
CYP2C9-inhibitor:	0.276
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.186
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	7.145
Half-life (T1/2):	0.592

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.653
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.11
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC470784

Natural Product ID:	NPC470784
*Common Name:**	PIWNJAZCHHBADQ-FEHLYQECSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PIWNJAZCHHBADQ-FEHLYQECSA-N
Standard InCHI:	InChI=1S/C22H27N3O6/c1-21(2,29)10-15-17-16(12-7-6-11(31-3)9-13(12)23-17)18(26)22(30)20(28)24-8-4-5-14(24)19(27)25(15)22/h6-7,9,14-15,18,23,26,29-30H,4-5,8,10H2,1-3H3/t14-,15-,18-,22-/m0/s1
SMILES:	COc1ccc2c(c1)[nH]c1c2[C@H](O)[C@]2(N([C@H]1CC(O)(C)C)C(=O)[C@H]1N(C2=O)CCC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229115
PubChem CID:	76318715
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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
MIC	8
Others	1

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	73.2	ug.mL-1	PMID[485809]
NPT1203	Organism	Fusarium graminearum	Fusarium graminearum	MIC	=	25.0	ug.mL-1	PMID[485809]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	MIC	=	50.0	ug.mL-1	PMID[485809]
NPT5164	Organism	Fusarium oxysporum f. sp. niveum	Fusarium oxysporum f. sp. niveum	MIC	=	25.0	ug.mL-1	PMID[485809]
NPT2600	Organism	Fusarium solani	Fusarium solani	MIC	=	50.0	ug.mL-1	PMID[485809]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	=	25.0	ug.mL-1	PMID[485809]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	25.0	ug.mL-1	PMID[485809]
NPT2705	Organism	Alternaria solani	Alternaria solani	MIC	=	25.0	ug.mL-1	PMID[485809]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	25.0	ug.mL-1	PMID[485809]

☑ 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 NPC470784 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	366
0.1-0.2	1936
0.2-0.3	11611
0.3-0.4	6977
0.4-0.5	15304
0.5-0.6	3544
0.6-0.7	2293
0.7-0.8	636
0.8-0.85	19
0.85-0.9	5
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9811	High Similarity	NPC470785
0.9764	High Similarity	NPC184680
0.9355	High Similarity	NPC474183
0.9143	High Similarity	NPC305984
0.9009	High Similarity	NPC303658
0.9009	High Similarity	NPC469594
0.9	High Similarity	NPC469592
0.9	High Similarity	NPC471080
0.8813	High Similarity	NPC194740
0.8545	High Similarity	NPC469589
0.8419	Intermediate Similarity	NPC189079
0.8394	Intermediate Similarity	NPC148183
0.8394	Intermediate Similarity	NPC152768
0.8341	Intermediate Similarity	NPC21638
0.8298	Intermediate Similarity	NPC133609
0.8166	Intermediate Similarity	NPC473105
0.8157	Intermediate Similarity	NPC475910
0.808	Intermediate Similarity	NPC128115
0.8009	Intermediate Similarity	NPC264176
0.7965	Intermediate Similarity	NPC60621
0.7949	Intermediate Similarity	NPC131486
0.7945	Intermediate Similarity	NPC260909
0.7922	Intermediate Similarity	NPC14288
0.7915	Intermediate Similarity	NPC475816
0.7913	Intermediate Similarity	NPC311906
0.7911	Intermediate Similarity	NPC473041
0.787	Intermediate Similarity	NPC261251
0.7857	Intermediate Similarity	NPC195788
0.7857	Intermediate Similarity	NPC237901
0.7854	Intermediate Similarity	NPC323752
0.7854	Intermediate Similarity	NPC323198
0.7848	Intermediate Similarity	NPC472098
0.7835	Intermediate Similarity	NPC100547
0.7835	Intermediate Similarity	NPC471762
0.7833	Intermediate Similarity	NPC91868
0.7833	Intermediate Similarity	NPC63971
0.7826	Intermediate Similarity	NPC24370
0.7826	Intermediate Similarity	NPC319232
0.7826	Intermediate Similarity	NPC214142
0.7824	Intermediate Similarity	NPC306376
0.7808	Intermediate Similarity	NPC476098
0.7802	Intermediate Similarity	NPC223409
0.7802	Intermediate Similarity	NPC95240
0.7802	Intermediate Similarity	NPC322135
0.7792	Intermediate Similarity	NPC118559
0.7792	Intermediate Similarity	NPC304307
0.7792	Intermediate Similarity	NPC124920
0.7792	Intermediate Similarity	NPC34580
0.7778	Intermediate Similarity	NPC244543
0.7763	Intermediate Similarity	NPC472099
0.7763	Intermediate Similarity	NPC150239
0.7752	Intermediate Similarity	NPC329747
0.7743	Intermediate Similarity	NPC330009
0.7735	Intermediate Similarity	NPC474192
0.7735	Intermediate Similarity	NPC475720
0.7735	Intermediate Similarity	NPC321592
0.7735	Intermediate Similarity	NPC54803
0.7725	Intermediate Similarity	NPC326363
0.7724	Intermediate Similarity	NPC284685
0.7722	Intermediate Similarity	NPC82472
0.7719	Intermediate Similarity	NPC213530
0.7719	Intermediate Similarity	NPC193267
0.7712	Intermediate Similarity	NPC473187
0.7708	Intermediate Similarity	NPC81939
0.7706	Intermediate Similarity	NPC122886
0.7705	Intermediate Similarity	NPC314882
0.7703	Intermediate Similarity	NPC270918
0.7695	Intermediate Similarity	NPC14812
0.7686	Intermediate Similarity	NPC323969
0.7682	Intermediate Similarity	NPC66777
0.7682	Intermediate Similarity	NPC295898
0.768	Intermediate Similarity	NPC315467
0.7679	Intermediate Similarity	NPC471304
0.7676	Intermediate Similarity	NPC475666
0.7675	Intermediate Similarity	NPC247803
0.7671	Intermediate Similarity	NPC249040
0.7654	Intermediate Similarity	NPC165964
0.7649	Intermediate Similarity	NPC478009
0.7647	Intermediate Similarity	NPC101350
0.7644	Intermediate Similarity	NPC87413
0.7639	Intermediate Similarity	NPC478078
0.7639	Intermediate Similarity	NPC110151
0.7632	Intermediate Similarity	NPC312645
0.7627	Intermediate Similarity	NPC284888
0.7619	Intermediate Similarity	NPC280272
0.7611	Intermediate Similarity	NPC258048
0.7609	Intermediate Similarity	NPC174760
0.7605	Intermediate Similarity	NPC235685
0.7602	Intermediate Similarity	NPC478080
0.76	Intermediate Similarity	NPC152620
0.7598	Intermediate Similarity	NPC96321
0.7595	Intermediate Similarity	NPC325976
0.7595	Intermediate Similarity	NPC245055
0.7595	Intermediate Similarity	NPC33064
0.7594	Intermediate Similarity	NPC84478
0.7593	Intermediate Similarity	NPC204970
0.7586	Intermediate Similarity	NPC122436
0.7581	Intermediate Similarity	NPC478006
0.7578	Intermediate Similarity	NPC472111
0.7578	Intermediate Similarity	NPC476106
0.7577	Intermediate Similarity	NPC151781
0.7577	Intermediate Similarity	NPC316181
0.7577	Intermediate Similarity	NPC89508
0.7577	Intermediate Similarity	NPC74562
0.7576	Intermediate Similarity	NPC198503
0.757	Intermediate Similarity	NPC315634
0.757	Intermediate Similarity	NPC100734
0.757	Intermediate Similarity	NPC88923
0.7569	Intermediate Similarity	NPC471303
0.7568	Intermediate Similarity	NPC223427
0.7564	Intermediate Similarity	NPC473185
0.7545	Intermediate Similarity	NPC249583
0.7542	Intermediate Similarity	NPC260434
0.7535	Intermediate Similarity	NPC175474
0.7534	Intermediate Similarity	NPC243834
0.7534	Intermediate Similarity	NPC70956
0.7533	Intermediate Similarity	NPC308137
0.7533	Intermediate Similarity	NPC310211
0.7532	Intermediate Similarity	NPC33949
0.7531	Intermediate Similarity	NPC184225
0.753	Intermediate Similarity	NPC303374
0.7522	Intermediate Similarity	NPC123976
0.7522	Intermediate Similarity	NPC264285
0.7522	Intermediate Similarity	NPC167860
0.7511	Intermediate Similarity	NPC329793
0.7511	Intermediate Similarity	NPC79129
0.7511	Intermediate Similarity	NPC81654
0.7511	Intermediate Similarity	NPC195461
0.7511	Intermediate Similarity	NPC249150
0.7511	Intermediate Similarity	NPC49196
0.7511	Intermediate Similarity	NPC313985
0.751	Intermediate Similarity	NPC478010
0.75	Intermediate Similarity	NPC277350
0.75	Intermediate Similarity	NPC478011
0.749	Intermediate Similarity	NPC78609
0.749	Intermediate Similarity	NPC272549
0.749	Intermediate Similarity	NPC477549
0.7489	Intermediate Similarity	NPC157931
0.7479	Intermediate Similarity	NPC179287
0.7478	Intermediate Similarity	NPC477160
0.7478	Intermediate Similarity	NPC169402
0.7477	Intermediate Similarity	NPC232727
0.7471	Intermediate Similarity	NPC314176
0.7468	Intermediate Similarity	NPC16352
0.7468	Intermediate Similarity	NPC475969
0.7468	Intermediate Similarity	NPC475859
0.7467	Intermediate Similarity	NPC4687
0.7467	Intermediate Similarity	NPC321428
0.7459	Intermediate Similarity	NPC469734
0.7458	Intermediate Similarity	NPC473183
0.7458	Intermediate Similarity	NPC6786
0.7457	Intermediate Similarity	NPC132642
0.7455	Intermediate Similarity	NPC285558
0.7454	Intermediate Similarity	NPC102338
0.7454	Intermediate Similarity	NPC63199
0.7454	Intermediate Similarity	NPC196251
0.7454	Intermediate Similarity	NPC111602
0.7453	Intermediate Similarity	NPC91179
0.7446	Intermediate Similarity	NPC46561
0.7444	Intermediate Similarity	NPC475085
0.7444	Intermediate Similarity	NPC291535
0.7444	Intermediate Similarity	NPC475112
0.7444	Intermediate Similarity	NPC199277
0.7444	Intermediate Similarity	NPC135887
0.7436	Intermediate Similarity	NPC475271
0.7435	Intermediate Similarity	NPC183407
0.7435	Intermediate Similarity	NPC469928
0.7435	Intermediate Similarity	NPC322064
0.7434	Intermediate Similarity	NPC39679
0.7431	Intermediate Similarity	NPC314056
0.7426	Intermediate Similarity	NPC470730
0.7426	Intermediate Similarity	NPC477175
0.7425	Intermediate Similarity	NPC477532
0.7425	Intermediate Similarity	NPC310118
0.7421	Intermediate Similarity	NPC50503
0.7421	Intermediate Similarity	NPC52557
0.7419	Intermediate Similarity	NPC472112
0.7414	Intermediate Similarity	NPC473179
0.7412	Intermediate Similarity	NPC23294
0.741	Intermediate Similarity	NPC191489
0.741	Intermediate Similarity	NPC89549
0.7393	Intermediate Similarity	NPC220851
0.7391	Intermediate Similarity	NPC116238
0.7389	Intermediate Similarity	NPC244741
0.7389	Intermediate Similarity	NPC88008
0.7384	Intermediate Similarity	NPC314954
0.7382	Intermediate Similarity	NPC272174
0.7381	Intermediate Similarity	NPC161861
0.738	Intermediate Similarity	NPC316981
0.7375	Intermediate Similarity	NPC39370
0.7375	Intermediate Similarity	NPC473184
0.7371	Intermediate Similarity	NPC174788
0.7368	Intermediate Similarity	NPC303951
0.7366	Intermediate Similarity	NPC477066
0.7366	Intermediate Similarity	NPC475844
0.7364	Intermediate Similarity	NPC469554
0.7364	Intermediate Similarity	NPC165743
0.7364	Intermediate Similarity	NPC473186
0.7364	Intermediate Similarity	NPC478012
0.736	Intermediate Similarity	NPC53534

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 NPC470784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	561
0.2-0.3	788
0.3-0.4	1368
0.4-0.5	2532
0.5-0.6	2519
0.6-0.7	1022
0.7-0.8	148
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8444	Intermediate Similarity	NPD4885	Approved
0.817	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD8460	Approved
0.7945	Intermediate Similarity	NPD8459	Approved
0.7915	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD3003	Approved
0.7857	Intermediate Similarity	NPD8465	Approved
0.7857	Intermediate Similarity	NPD8467	Approved
0.7857	Intermediate Similarity	NPD8466	Approved
0.7828	Intermediate Similarity	NPD5658	Approved
0.7802	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7194	Discontinued
0.7788	Intermediate Similarity	NPD1768	Approved
0.776	Intermediate Similarity	NPD8364	Approved
0.776	Intermediate Similarity	NPD8363	Approved
0.7749	Intermediate Similarity	NPD7426	Phase 1
0.7735	Intermediate Similarity	NPD7796	Approved
0.7735	Intermediate Similarity	NPD7797	Approved
0.7734	Intermediate Similarity	NPD8426	Approved
0.7734	Intermediate Similarity	NPD8425	Approved
0.7724	Intermediate Similarity	NPD7956	Approved
0.7724	Intermediate Similarity	NPD7955	Approved
0.7717	Intermediate Similarity	NPD8429	Approved
0.7717	Intermediate Similarity	NPD8427	Approved
0.7717	Intermediate Similarity	NPD8428	Approved
0.7709	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD5902	Approved
0.7699	Intermediate Similarity	NPD5903	Approved
0.7698	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7675	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7558	Phase 2
0.7621	Intermediate Similarity	NPD4897	Phase 2
0.76	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2916	Discontinued
0.7578	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD7803	Approved
0.7553	Intermediate Similarity	NPD4373	Phase 2
0.7552	Intermediate Similarity	NPD6517	Phase 3
0.7545	Intermediate Similarity	NPD1392	Approved
0.7542	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8016	Phase 3
0.7522	Intermediate Similarity	NPD5632	Approved
0.7522	Intermediate Similarity	NPD6985	Discontinued
0.7521	Intermediate Similarity	NPD7603	Discontinued
0.7511	Intermediate Similarity	NPD4601	Approved
0.7511	Intermediate Similarity	NPD4600	Approved
0.751	Intermediate Similarity	NPD5482	Discontinued
0.75	Intermediate Similarity	NPD8255	Phase 2
0.7489	Intermediate Similarity	NPD7470	Discontinued
0.7467	Intermediate Similarity	NPD5293	Phase 2
0.7438	Intermediate Similarity	NPD6790	Phase 1
0.7426	Intermediate Similarity	NPD4952	Phase 3
0.7425	Intermediate Similarity	NPD5506	Approved
0.7425	Intermediate Similarity	NPD5507	Approved
0.7418	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8489	Phase 1
0.741	Intermediate Similarity	NPD7708	Approved
0.7407	Intermediate Similarity	NPD6716	Phase 1
0.7388	Intermediate Similarity	NPD8359	Phase 2
0.7387	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5559	Phase 2
0.7378	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5003	Discontinued
0.7359	Intermediate Similarity	NPD5612	Discontinued
0.7354	Intermediate Similarity	NPD4500	Approved
0.7354	Intermediate Similarity	NPD4501	Approved
0.7353	Intermediate Similarity	NPD5479	Discontinued
0.7349	Intermediate Similarity	NPD8463	Approved
0.7349	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD4502	Phase 2
0.7328	Intermediate Similarity	NPD4558	Phase 2
0.7322	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7181	Phase 3
0.7313	Intermediate Similarity	NPD7222	Phase 2
0.7309	Intermediate Similarity	NPD6248	Phase 2
0.7309	Intermediate Similarity	NPD6249	Phase 2
0.7287	Intermediate Similarity	NPD8358	Approved
0.7285	Intermediate Similarity	NPD4602	Approved
0.7285	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4203	Approved
0.7256	Intermediate Similarity	NPD4204	Approved
0.7243	Intermediate Similarity	NPD4368	Phase 2
0.7243	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7859	Phase 2
0.7229	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5450	Discontinued
0.7227	Intermediate Similarity	NPD8284	Discontinued
0.7227	Intermediate Similarity	NPD3263	Phase 3
0.7222	Intermediate Similarity	NPD6568	Discontinued
0.7205	Intermediate Similarity	NPD6376	Discontinued
0.7197	Intermediate Similarity	NPD3259	Approved
0.7194	Intermediate Similarity	NPD8091	Phase 3
0.7182	Intermediate Similarity	NPD2564	Approved
0.7182	Intermediate Similarity	NPD2565	Phase 2
0.7178	Intermediate Similarity	NPD6962	Phase 2
0.7175	Intermediate Similarity	NPD5512	Phase 3
0.7173	Intermediate Similarity	NPD6209	Approved
0.7173	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7453	Approved
0.7162	Intermediate Similarity	NPD1038	Approved
0.7162	Intermediate Similarity	NPD7452	Approved
0.7155	Intermediate Similarity	NPD5640	Discontinued
0.7149	Intermediate Similarity	NPD4033	Approved
0.7149	Intermediate Similarity	NPD4038	Approved
0.7149	Intermediate Similarity	NPD4035	Approved
0.7149	Intermediate Similarity	NPD4037	Approved
0.7149	Intermediate Similarity	NPD31	Approved
0.7149	Intermediate Similarity	NPD4034	Approved
0.7149	Intermediate Similarity	NPD32	Approved
0.7149	Intermediate Similarity	NPD4036	Approved
0.7149	Intermediate Similarity	NPD7031	Phase 1
0.7149	Intermediate Similarity	NPD4039	Approved
0.7149	Intermediate Similarity	NPD4122	Approved
0.7137	Intermediate Similarity	NPD6531	Approved
0.7137	Intermediate Similarity	NPD6530	Approved
0.7131	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7853	Phase 2
0.713	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD484	Approved
0.7115	Intermediate Similarity	NPD8247	Approved
0.7115	Intermediate Similarity	NPD8246	Approved
0.7112	Intermediate Similarity	NPD5067	Phase 2
0.7112	Intermediate Similarity	NPD5066	Phase 2
0.7105	Intermediate Similarity	NPD5487	Phase 1
0.7101	Intermediate Similarity	NPD6995	Phase 1
0.7091	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6242	Discontinued
0.708	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4795	Phase 2
0.7073	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD3006	Discontinued
0.7054	Intermediate Similarity	NPD7731	Approved
0.7054	Intermediate Similarity	NPD4328	Approved
0.7054	Intermediate Similarity	NPD7730	Approved
0.7049	Intermediate Similarity	NPD7790	Approved
0.7049	Intermediate Similarity	NPD7791	Approved
0.7049	Intermediate Similarity	NPD7950	Approved
0.7049	Intermediate Similarity	NPD7951	Approved
0.7049	Intermediate Similarity	NPD7789	Approved
0.7049	Intermediate Similarity	NPD7952	Approved
0.7049	Intermediate Similarity	NPD7953	Approved
0.7043	Intermediate Similarity	NPD8403	Phase 1
0.7043	Intermediate Similarity	NPD3507	Phase 2
0.7042	Intermediate Similarity	NPD7271	Approved
0.704	Intermediate Similarity	NPD5488	Discontinued
0.7038	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7219	Approved
0.7029	Intermediate Similarity	NPD7221	Approved
0.7022	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2383	Phase 1
0.7012	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7675	Phase 3
0.7012	Intermediate Similarity	NPD7674	Phase 3
0.7012	Intermediate Similarity	NPD8289	Discontinued
0.7009	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD2176	Approved
0.7004	Intermediate Similarity	NPD2175	Phase 3
0.7004	Intermediate Similarity	NPD2177	Approved
0.7	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7824	Approved
0.6991	Remote Similarity	NPD7948	Phase 1
0.6991	Remote Similarity	NPD6206	Phase 1
0.6986	Remote Similarity	NPD5596	Phase 2
0.6986	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2510	Approved
0.6983	Remote Similarity	NPD7994	Phase 2
0.6983	Remote Similarity	NPD2509	Approved
0.6982	Remote Similarity	NPD4334	Discontinued
0.698	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3243	Approved
0.6978	Remote Similarity	NPD4418	Discontinued
0.6975	Remote Similarity	NPD3258	Approved
0.6974	Remote Similarity	NPD1739	Approved
0.6974	Remote Similarity	NPD1740	Approved
0.697	Remote Similarity	NPD5530	Phase 1
0.697	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5256	Discontinued
0.6967	Remote Similarity	NPD7688	Phase 1
0.6966	Remote Similarity	NPD3570	Phase 2
0.6966	Remote Similarity	NPD5416	Discontinued
0.6964	Remote Similarity	NPD6569	Phase 2
0.696	Remote Similarity	NPD6261	Phase 3
0.6958	Remote Similarity	NPD8356	Approved
0.6955	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2951	Discontinued
0.6951	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8479	Phase 2
0.694	Remote Similarity	NPD8322	Phase 2
0.6936	Remote Similarity	NPD7594	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