NPASS Compound

Structure

NPC469589 OpenBabel07101719132D 33 37 0 0 1 0 0 0 0 0999 V2000 3.6102 -3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2574 -2.6270 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 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0734 2.5361 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 3.9703 -1.4680 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 2.9921 -1.2601 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 4.2654 0.6045 0.0000 C 0 0 0 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 4.2793 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 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 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 N 0 0 3 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 0.0000 0.0000 0.0000 N 0 0 3 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 0.0000 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 33 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 19 1 0 0 0 0 8 9 2 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 19 1 0 0 0 0 15 30 1 0 0 0 0 16 27 1 0 0 0 0 16 28 1 0 0 0 0 19 28 1 6 0 0 0 20 33 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 30 1 6 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 25 29 1 0 0 0 0 26 27 1 1 0 0 0 26 31 1 0 0 0 0 27 30 1 6 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	451.28
Volume:	476.308
LogP:	4.922
LogD:	4.071
LogS:	-3.28
# Rotatable Bonds:	4
TPSA:	61.1
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	4.547
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.844
MDCK Permeability:	1.2487365893321112e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.919
Human Intestinal Absorption (HIA):	0.268
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	82.679443359375%
Volume Distribution (VD):	1.874
Pgp-substrate:	10.367673873901367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.416
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.665
CYP3A4-inhibitor:	0.808
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	12.994
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.771
Human Hepatotoxicity (H-HT):	0.996
Drug-inuced Liver Injury (DILI):	0.154
AMES Toxicity:	0.779
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.093
Carcinogencity:	0.783
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC469589

Natural Product ID:	NPC469589
*Common Name:**	Fumitremorgin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WKDABLWSPHOACG-DKNHICIASA-N
Standard InCHI:	InChI=1S/C27H37N3O3/c1-17(2)10-12-29-22-14-20(33-5)8-9-21(22)24-25(29)23(13-18(3)4)30-15-19-7-6-11-28(19)16-27(30,32)26(24)31/h8-10,13-14,19,23,26,31-32H,6-7,11-12,15-16H2,1-5H3/t19-,23-,26-,27+/m0/s1
SMILES:	COc1ccc2c(c1)n(CC=C(C)C)c1c2[C@H](O)[C@]2(N([C@H]1C=C(C)C)C[C@H]1N(C2)CCC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1089482
PubChem CID:	46885607
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
IC50	4
MIC	8
Others	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	13
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT470	Individual Protein	Rhodesain	Trypanosoma brucei rhodesiense	IC50	=	8500.0	nM	PMID[462892]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	104000.0	nM	PMID[462892]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	19500.0	nM	PMID[462892]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[462892]
NPT2	Others	Unspecified		Ratio IC50	=	5.3	uM	PMID[462892]
NPT27	Others	Unspecified		Activity	=	3.3	uM	PMID[462892]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	5.0	mg kg-1	PMID[462892]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	70.0	%	PMID[462892]
NPT1769	Organism	Mythimna separata	Mythimna separata	AFI	=	50.0	%	PMID[462893]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	13.6	ug.mL-1	PMID[462893]
NPT1203	Organism	Fusarium graminearum	Fusarium graminearum	MIC	=	12.5	ug.mL-1	PMID[462893]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	MIC	=	50.0	ug.mL-1	PMID[462893]
NPT5164	Organism	Fusarium oxysporum f. sp. niveum	Fusarium oxysporum f. sp. niveum	MIC	=	25.0	ug.mL-1	PMID[462893]
NPT2600	Organism	Fusarium solani	Fusarium solani	MIC	=	100.0	ug.mL-1	PMID[462893]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	=	12.5	ug.mL-1	PMID[462893]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	6.25	ug.mL-1	PMID[462893]
NPT2705	Organism	Alternaria solani	Alternaria solani	MIC	=	6.25	ug.mL-1	PMID[462893]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	MIC	=	6.25	ug.mL-1	PMID[462893]

☑ 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 NPC469589 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	422
0.1-0.2	1918
0.2-0.3	12365
0.3-0.4	6668
0.4-0.5	14524
0.5-0.6	3859
0.6-0.7	2355
0.7-0.8	563
0.8-0.85	17
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC469592
0.9479	High Similarity	NPC471080
0.9286	High Similarity	NPC469594
0.881	High Similarity	NPC474183
0.8724	High Similarity	NPC472111
0.8545	High Similarity	NPC470784
0.8543	High Similarity	NPC475910
0.8411	Intermediate Similarity	NPC184680
0.8374	Intermediate Similarity	NPC264176
0.8372	Intermediate Similarity	NPC470785
0.8213	Intermediate Similarity	NPC305984
0.8195	Intermediate Similarity	NPC472098
0.8173	Intermediate Similarity	NPC303658
0.8134	Intermediate Similarity	NPC193267
0.8134	Intermediate Similarity	NPC213530
0.8119	Intermediate Similarity	NPC165349
0.8119	Intermediate Similarity	NPC274291
0.8119	Intermediate Similarity	NPC264166
0.8119	Intermediate Similarity	NPC47059
0.8119	Intermediate Similarity	NPC329708
0.8119	Intermediate Similarity	NPC118832
0.8105	Intermediate Similarity	NPC133261
0.81	Intermediate Similarity	NPC329747
0.8037	Intermediate Similarity	NPC473185
0.802	Intermediate Similarity	NPC295898
0.8019	Intermediate Similarity	NPC280272
0.801	Intermediate Similarity	NPC249040
0.799	Intermediate Similarity	NPC475841
0.799	Intermediate Similarity	NPC474145
0.798	Intermediate Similarity	NPC475774
0.7961	Intermediate Similarity	NPC174758
0.7938	Intermediate Similarity	NPC84478
0.7938	Intermediate Similarity	NPC62069
0.7933	Intermediate Similarity	NPC112206
0.7933	Intermediate Similarity	NPC202605
0.7925	Intermediate Similarity	NPC132642
0.7923	Intermediate Similarity	NPC167860
0.7923	Intermediate Similarity	NPC123976
0.7913	Intermediate Similarity	NPC470931
0.7909	Intermediate Similarity	NPC473183
0.7905	Intermediate Similarity	NPC148183
0.7905	Intermediate Similarity	NPC152768
0.7892	Intermediate Similarity	NPC223427
0.7889	Intermediate Similarity	NPC79293
0.7889	Intermediate Similarity	NPC279401
0.7882	Intermediate Similarity	NPC232727
0.787	Intermediate Similarity	NPC110151
0.7865	Intermediate Similarity	NPC326575
0.7861	Intermediate Similarity	NPC70956
0.7861	Intermediate Similarity	NPC243834
0.786	Intermediate Similarity	NPC21638
0.7854	Intermediate Similarity	NPC285558
0.785	Intermediate Similarity	NPC162748
0.784	Intermediate Similarity	NPC128115
0.7834	Intermediate Similarity	NPC314954
0.7834	Intermediate Similarity	NPC194740
0.7833	Intermediate Similarity	NPC329793
0.782	Intermediate Similarity	NPC183407
0.7818	Intermediate Similarity	NPC473184
0.7816	Intermediate Similarity	NPC476106
0.7812	Intermediate Similarity	NPC24594
0.7812	Intermediate Similarity	NPC472122
0.7812	Intermediate Similarity	NPC134586
0.7803	Intermediate Similarity	NPC99891
0.7788	Intermediate Similarity	NPC174672
0.7773	Intermediate Similarity	NPC473105
0.7772	Intermediate Similarity	NPC283152
0.7772	Intermediate Similarity	NPC211997
0.7767	Intermediate Similarity	NPC476581
0.7767	Intermediate Similarity	NPC16452
0.7767	Intermediate Similarity	NPC36229
0.7762	Intermediate Similarity	NPC316981
0.7757	Intermediate Similarity	NPC472099
0.7757	Intermediate Similarity	NPC477533
0.7756	Intermediate Similarity	NPC199277
0.7756	Intermediate Similarity	NPC135887
0.7749	Intermediate Similarity	NPC158129
0.7746	Intermediate Similarity	NPC173080
0.7736	Intermediate Similarity	NPC274982
0.7727	Intermediate Similarity	NPC469554
0.7721	Intermediate Similarity	NPC310118
0.771	Intermediate Similarity	NPC473179
0.7703	Intermediate Similarity	NPC295228
0.7696	Intermediate Similarity	NPC476582
0.7696	Intermediate Similarity	NPC476578
0.7696	Intermediate Similarity	NPC4071
0.7692	Intermediate Similarity	NPC472105
0.7692	Intermediate Similarity	NPC187827
0.7685	Intermediate Similarity	NPC267928
0.7682	Intermediate Similarity	NPC475253
0.7678	Intermediate Similarity	NPC202768
0.7678	Intermediate Similarity	NPC296482
0.7678	Intermediate Similarity	NPC203168
0.7678	Intermediate Similarity	NPC171409
0.7678	Intermediate Similarity	NPC53069
0.7678	Intermediate Similarity	NPC94157
0.7678	Intermediate Similarity	NPC96405
0.7676	Intermediate Similarity	NPC26872
0.767	Intermediate Similarity	NPC475085
0.767	Intermediate Similarity	NPC475112
0.767	Intermediate Similarity	NPC291535
0.7667	Intermediate Similarity	NPC11464
0.7659	Intermediate Similarity	NPC11017
0.7653	Intermediate Similarity	NPC170114
0.7647	Intermediate Similarity	NPC26850
0.7642	Intermediate Similarity	NPC478074
0.7641	Intermediate Similarity	NPC72980
0.7639	Intermediate Similarity	NPC477532
0.7639	Intermediate Similarity	NPC60621
0.7635	Intermediate Similarity	NPC251090
0.7633	Intermediate Similarity	NPC53144
0.7621	Intermediate Similarity	NPC31930
0.7619	Intermediate Similarity	NPC177404
0.7619	Intermediate Similarity	NPC476116
0.7614	Intermediate Similarity	NPC472109
0.7614	Intermediate Similarity	NPC472110
0.761	Intermediate Similarity	NPC18487
0.7608	Intermediate Similarity	NPC53344
0.7608	Intermediate Similarity	NPC135549
0.7608	Intermediate Similarity	NPC313189
0.7608	Intermediate Similarity	NPC193777
0.7606	Intermediate Similarity	NPC470549
0.76	Intermediate Similarity	NPC477861
0.7591	Intermediate Similarity	NPC253580
0.7588	Intermediate Similarity	NPC204385
0.7583	Intermediate Similarity	NPC219664
0.7583	Intermediate Similarity	NPC5145
0.7581	Intermediate Similarity	NPC473041
0.7577	Intermediate Similarity	NPC312872
0.7573	Intermediate Similarity	NPC315957
0.7571	Intermediate Similarity	NPC82548
0.7571	Intermediate Similarity	NPC287208
0.7563	Intermediate Similarity	NPC219963
0.7561	Intermediate Similarity	NPC72211
0.7559	Intermediate Similarity	NPC266931
0.755	Intermediate Similarity	NPC46580
0.755	Intermediate Similarity	NPC66083
0.7545	Intermediate Similarity	NPC470126
0.7538	Intermediate Similarity	NPC203754
0.7538	Intermediate Similarity	NPC288943
0.7538	Intermediate Similarity	NPC42591
0.7538	Intermediate Similarity	NPC150048
0.7537	Intermediate Similarity	NPC307963
0.7525	Intermediate Similarity	NPC176127
0.7513	Intermediate Similarity	NPC15840
0.7512	Intermediate Similarity	NPC470500
0.7512	Intermediate Similarity	NPC26679
0.7511	Intermediate Similarity	NPC476997
0.7511	Intermediate Similarity	NPC469734
0.75	Intermediate Similarity	NPC214980
0.75	Intermediate Similarity	NPC131017
0.75	Intermediate Similarity	NPC66815
0.7489	Intermediate Similarity	NPC101543
0.7488	Intermediate Similarity	NPC477019
0.7488	Intermediate Similarity	NPC19872
0.7488	Intermediate Similarity	NPC8022
0.7488	Intermediate Similarity	NPC234197
0.7488	Intermediate Similarity	NPC176538
0.7488	Intermediate Similarity	NPC195268
0.7488	Intermediate Similarity	NPC133140
0.7488	Intermediate Similarity	NPC470799
0.7477	Intermediate Similarity	NPC476998
0.7477	Intermediate Similarity	NPC476996
0.7475	Intermediate Similarity	NPC314394
0.7474	Intermediate Similarity	NPC255229
0.7474	Intermediate Similarity	NPC81229
0.7467	Intermediate Similarity	NPC472434
0.7464	Intermediate Similarity	NPC162484
0.7464	Intermediate Similarity	NPC200836
0.7463	Intermediate Similarity	NPC70259
0.7463	Intermediate Similarity	NPC13880
0.7461	Intermediate Similarity	NPC317430
0.7455	Intermediate Similarity	NPC473182
0.745	Intermediate Similarity	NPC62510
0.744	Intermediate Similarity	NPC287437
0.744	Intermediate Similarity	NPC128823
0.7438	Intermediate Similarity	NPC469390
0.7438	Intermediate Similarity	NPC92111
0.7437	Intermediate Similarity	NPC139291
0.7437	Intermediate Similarity	NPC472108
0.7432	Intermediate Similarity	NPC476994
0.743	Intermediate Similarity	NPC48353
0.7425	Intermediate Similarity	NPC189079
0.7421	Intermediate Similarity	NPC2497
0.7418	Intermediate Similarity	NPC471304
0.7418	Intermediate Similarity	NPC85273
0.7418	Intermediate Similarity	NPC290689
0.7415	Intermediate Similarity	NPC205934
0.7415	Intermediate Similarity	NPC43787
0.7413	Intermediate Similarity	NPC314573
0.7407	Intermediate Similarity	NPC330009
0.7402	Intermediate Similarity	NPC141915
0.7402	Intermediate Similarity	NPC114335
0.7402	Intermediate Similarity	NPC280964
0.7395	Intermediate Similarity	NPC162530
0.7393	Intermediate Similarity	NPC472287
0.7393	Intermediate Similarity	NPC472286
0.7391	Intermediate Similarity	NPC81939
0.7389	Intermediate Similarity	NPC76748
0.7387	Intermediate Similarity	NPC266551

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 NPC469589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	590
0.2-0.3	821
0.3-0.4	1142
0.4-0.5	2497
0.5-0.6	2589
0.6-0.7	1078
0.7-0.8	210
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8492	Intermediate Similarity	NPD7222	Phase 2
0.8308	Intermediate Similarity	NPD7453	Approved
0.8308	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD7452	Approved
0.8259	Intermediate Similarity	NPD3003	Approved
0.8211	Intermediate Similarity	NPD4203	Approved
0.8211	Intermediate Similarity	NPD4204	Approved
0.8177	Intermediate Similarity	NPD5658	Approved
0.8177	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1768	Approved
0.8134	Intermediate Similarity	NPD7194	Discontinued
0.8119	Intermediate Similarity	NPD4039	Approved
0.8119	Intermediate Similarity	NPD4033	Approved
0.8119	Intermediate Similarity	NPD4037	Approved
0.8119	Intermediate Similarity	NPD4035	Approved
0.8119	Intermediate Similarity	NPD31	Approved
0.8119	Intermediate Similarity	NPD4122	Approved
0.8119	Intermediate Similarity	NPD32	Approved
0.8119	Intermediate Similarity	NPD4036	Approved
0.8119	Intermediate Similarity	NPD4038	Approved
0.8119	Intermediate Similarity	NPD4034	Approved
0.8018	Intermediate Similarity	NPD7558	Phase 2
0.7951	Intermediate Similarity	NPD1392	Approved
0.7943	Intermediate Similarity	NPD5902	Approved
0.7943	Intermediate Similarity	NPD5903	Approved
0.7929	Intermediate Similarity	NPD6569	Phase 2
0.7908	Intermediate Similarity	NPD2383	Phase 1
0.7907	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7675	Phase 3
0.7907	Intermediate Similarity	NPD7674	Phase 3
0.785	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD6985	Discontinued
0.7824	Intermediate Similarity	NPD7426	Phase 1
0.7816	Intermediate Similarity	NPD5530	Phase 1
0.7799	Intermediate Similarity	NPD4502	Phase 2
0.7767	Intermediate Similarity	NPD4795	Phase 2
0.7761	Intermediate Similarity	NPD4418	Discontinued
0.77	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD6246	Approved
0.7679	Intermediate Similarity	NPD8016	Phase 3
0.7679	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD3815	Phase 1
0.7678	Intermediate Similarity	NPD3816	Phase 1
0.7653	Intermediate Similarity	NPD5612	Discontinued
0.7644	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3570	Phase 2
0.7626	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7219	Approved
0.7604	Intermediate Similarity	NPD7221	Approved
0.7591	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6590	Discontinued
0.7573	Intermediate Similarity	NPD1739	Approved
0.7573	Intermediate Similarity	NPD1740	Approved
0.7568	Intermediate Similarity	NPD7797	Approved
0.7568	Intermediate Similarity	NPD7796	Approved
0.7563	Intermediate Similarity	NPD3037	Phase 1
0.7551	Intermediate Similarity	NPD3920	Phase 2
0.7549	Intermediate Similarity	NPD3477	Phase 2
0.7549	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3875	Discontinued
0.7537	Intermediate Similarity	NPD1038	Approved
0.7524	Intermediate Similarity	NPD2176	Approved
0.7524	Intermediate Similarity	NPD2175	Phase 3
0.7524	Intermediate Similarity	NPD2177	Approved
0.7523	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD8359	Phase 2
0.75	Intermediate Similarity	NPD5256	Discontinued
0.7489	Intermediate Similarity	NPD4885	Approved
0.7488	Intermediate Similarity	NPD3922	Approved
0.7488	Intermediate Similarity	NPD3921	Approved
0.7488	Intermediate Similarity	NPD3924	Approved
0.7488	Intermediate Similarity	NPD3923	Approved
0.7477	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5066	Phase 2
0.7465	Intermediate Similarity	NPD5067	Phase 2
0.7464	Intermediate Similarity	NPD6991	Approved
0.7463	Intermediate Similarity	NPD5512	Phase 3
0.7463	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1034	Phase 3
0.7455	Intermediate Similarity	NPD6494	Phase 2
0.7418	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6159	Phase 2
0.7406	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD8403	Phase 1
0.7387	Intermediate Similarity	NPD3259	Approved
0.7387	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8364	Approved
0.7386	Intermediate Similarity	NPD8363	Approved
0.738	Intermediate Similarity	NPD6517	Phase 3
0.7366	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4897	Phase 2
0.736	Intermediate Similarity	NPD2381	Approved
0.736	Intermediate Similarity	NPD2380	Approved
0.736	Intermediate Similarity	NPD2382	Approved
0.7353	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD5930	Phase 3
0.7348	Intermediate Similarity	NPD7068	Approved
0.7348	Intermediate Similarity	NPD7067	Approved
0.7343	Intermediate Similarity	NPD7948	Phase 1
0.7339	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7112	Discontinued
0.7325	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7672	Approved
0.7324	Intermediate Similarity	NPD2916	Discontinued
0.7324	Intermediate Similarity	NPD7671	Approved
0.7311	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6500	Approved
0.7306	Intermediate Similarity	NPD6501	Approved
0.7306	Intermediate Similarity	NPD3763	Approved
0.7304	Intermediate Similarity	NPD6716	Phase 1
0.7302	Intermediate Similarity	NPD5939	Approved
0.7302	Intermediate Similarity	NPD2540	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5936	Approved
0.7301	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6550	Discontinued
0.7291	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6962	Phase 2
0.7286	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1856	Discontinued
0.7282	Intermediate Similarity	NPD4551	Phase 2
0.7277	Intermediate Similarity	NPD6227	Discontinued
0.7269	Intermediate Similarity	NPD7069	Discontinued
0.7264	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD3397	Phase 2
0.726	Intermediate Similarity	NPD5632	Approved
0.726	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD2882	Phase 1
0.7246	Intermediate Similarity	NPD3396	Approved
0.7246	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3395	Approved
0.7245	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7567	Approved
0.724	Intermediate Similarity	NPD7726	Phase 1
0.724	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6326	Phase 2
0.7232	Intermediate Similarity	NPD6327	Phase 1
0.7227	Intermediate Similarity	NPD6455	Phase 3
0.7225	Intermediate Similarity	NPD4080	Discontinued
0.7225	Intermediate Similarity	NPD4373	Phase 2
0.7222	Intermediate Similarity	NPD6220	Phase 3
0.722	Intermediate Similarity	NPD7719	Discontinued
0.722	Intermediate Similarity	NPD8063	Discontinued
0.7217	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7956	Approved
0.7197	Intermediate Similarity	NPD7955	Approved
0.7196	Intermediate Similarity	NPD6290	Phase 2
0.7195	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4548	Discontinued
0.7188	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7417	Discontinued
0.7185	Intermediate Similarity	NPD8244	Phase 2
0.7185	Intermediate Similarity	NPD8255	Phase 2
0.7183	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5596	Phase 2
0.7177	Intermediate Similarity	NPD6988	Phase 1
0.7177	Intermediate Similarity	NPD1622	Discontinued
0.7173	Intermediate Similarity	NPD8463	Approved
0.7171	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4602	Approved
0.7162	Intermediate Similarity	NPD5507	Approved
0.7162	Intermediate Similarity	NPD5506	Approved
0.7158	Intermediate Similarity	NPD6158	Phase 2
0.7158	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4375	Approved
0.7156	Intermediate Similarity	NPD5944	Phase 1
0.7156	Intermediate Similarity	NPD6978	Phase 2
0.7156	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5945	Phase 1
0.715	Intermediate Similarity	NPD5255	Approved
0.715	Intermediate Similarity	NPD1032	Phase 2
0.7143	Intermediate Similarity	NPD4131	Phase 3
0.7143	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD8467	Approved
0.7137	Intermediate Similarity	NPD8466	Approved
0.7137	Intermediate Similarity	NPD8465	Approved
0.7131	Intermediate Similarity	NPD7859	Phase 2
0.713	Intermediate Similarity	NPD1954	Phase 1
0.7129	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7555	Discontinued
0.7124	Intermediate Similarity	NPD5559	Phase 2

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