NPASS Compound

Structure

CID189609 OpenBabel06191715572D 26 28 0 0 1 0 0 0 0 0999 V2000 1.6269 -3.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0446 -4.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5058 -1.8035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1754 -1.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6324 -3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 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 0.2257 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3669 2.2653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5227 -0.5759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7688 -2.5316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8387 -0.6034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 -1.8271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 5 11 2 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 7 19 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 12 26 1 0 0 0 0 13 5 1 1 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 1 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 10 1 6 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 4 1 1 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.12
Volume:	354.587
LogP:	1.478
LogD:	1.428
LogS:	-3.007
# Rotatable Bonds:	4
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.601
Synthetic Accessibility Score:	6.112
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.853
MDCK Permeability:	1.917428380693309e-05
Pgp-inhibitor:	0.315
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	71.85697174072266%
Volume Distribution (VD):	1.026
Pgp-substrate:	39.39594650268555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.629
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.252
CYP3A4-substrate:	0.597

ADMET: Excretion

Clearance (CL):	7.569
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.261
Skin Sensitization:	0.959
Carcinogencity:	0.539
Eye Corrosion:	0.896
Eye Irritation:	0.965
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC189609

Natural Product ID:	NPC189609
*Common Name:**	Goiazensolide
IUPAC Name:	n.a.
Synonyms:	Goiazensolide; Goyazensolide
Standard InCHIKey:	HTMCLLSRQWRPTN-OKMRAYSCSA-N
Standard InCHI:	InChI=1S/C19H20O7/c1-9(2)17(22)25-14-7-19(4)15(21)6-12(26-19)11(8-20)5-13-16(14)10(3)18(23)24-13/h5-6,13-14,16,20H,1,3,7-8H2,2,4H3/b11-5-/t13-,14+,16+,19-/m1/s1
SMILES:	C=C(C)C(=O)O[C@H]1C[C@]2(C)C(=O)C=C(/C(=C[C@@H]3[C@@H]1C(=C)C(=O)O3)/CO)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL371358
PubChem CID:	5358393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO701	Lychnophora diamantinana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO6743	Piptocoma rufescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[29350920]
NPO5429	Vachellia pennatula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9855	Oricia gabonensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10254	Melaleuca cuticularis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6743	Piptocoma rufescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO701	Lychnophora diamantinana	Species	Asteraceae	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	14
MIC	1
Others	35

Activity Type	# Activity
Cell Line	30
Individual Protein	3
Organism	4
Others	3
Protein Complex	2
SINGLE PROTEIN	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	0.42	uM	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	0.56	uM	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	81.8	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	14.7	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	3.18	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	0.392	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	2.54	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	0.958	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	94.6	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	1.86	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	0.135	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	0.203	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	97.7	%	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	Activity	=	1.96	%	PMID[520349]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	560.0	nM	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	IC50	=	1100.0	nM	PMID[520349]
NPT6530	Cell Line	MOLM-13	Homo sapiens	IC50	=	860.0	nM	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	91.7	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	1.84	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	6.18	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	0.306	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	3.99	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	0.281	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	93.3	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	2.4	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	0.01	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	0.0	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	99.8	%	PMID[520349]
NPT2132	Cell Line	EOL1	Homo sapiens	Activity	=	0.189	%	PMID[520349]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	560.0	nM	PMID[520351]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	20.0	uM	PMID[520345]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.3	n.a.	PMID[520345]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	20.0	uM	PMID[520346]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	3.1	ug.mL-1	PMID[520347]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	625.17	nM	PMID[520348]
NPT27	Others	Unspecified		IC50	=	10050.0	nM	PMID[520348]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	630.0	nM	PMID[520348]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	IC50	=	155800.0	nM	PMID[520350]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	IC50	=	158489.32	nM	PMID[520350]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	Delta Tm	=	-0.32	degrees C	PMID[520350]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	Delta Tm	=	-0.84	degrees C	PMID[520350]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	Delta Tm	=	-1.13	degrees C	PMID[520350]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	Delta Tm	=	-0.73	degrees C	PMID[520350]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	Delta Tm	=	-4.19	degrees C	PMID[520350]
NPT21851	SINGLE PROTEIN	Dihydroorotate dehydrogenase (fumarate)	Leishmania major	Delta Tm	=	-6.51	degrees C	PMID[520350]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	1080.0	nM	PMID[520350]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	70.0	nM	PMID[520350]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	450.0	nM	PMID[520350]
NPT2	Others	Unspecified		IC50	=	1000.0	nM	PMID[520351]

☑ 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 NPC189609 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	211
0.1-0.2	1168
0.2-0.3	4125
0.3-0.4	7874
0.4-0.5	16205
0.5-0.6	8203
0.6-0.7	3818
0.7-0.8	1017
0.8-0.85	63
0.85-0.9	2
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC197835
1.0	High Similarity	NPC303653
1.0	High Similarity	NPC291500
1.0	High Similarity	NPC140591
0.9468	High Similarity	NPC301596
0.9468	High Similarity	NPC299396
0.9263	High Similarity	NPC172998
0.9208	High Similarity	NPC38154
0.9158	High Similarity	NPC273197
0.9158	High Similarity	NPC234339
0.866	High Similarity	NPC474338
0.85	High Similarity	NPC187268
0.8438	Intermediate Similarity	NPC295312
0.8421	Intermediate Similarity	NPC160138
0.84	Intermediate Similarity	NPC471462
0.8384	Intermediate Similarity	NPC304886
0.8367	Intermediate Similarity	NPC125674
0.8367	Intermediate Similarity	NPC475838
0.8367	Intermediate Similarity	NPC228451
0.8367	Intermediate Similarity	NPC59646
0.8351	Intermediate Similarity	NPC144133
0.8351	Intermediate Similarity	NPC179394
0.8351	Intermediate Similarity	NPC475855
0.8283	Intermediate Similarity	NPC474247
0.8283	Intermediate Similarity	NPC469632
0.8283	Intermediate Similarity	NPC470521
0.8182	Intermediate Similarity	NPC475912
0.8163	Intermediate Similarity	NPC3436
0.8155	Intermediate Similarity	NPC185141
0.8155	Intermediate Similarity	NPC128733
0.8155	Intermediate Similarity	NPC476270
0.8155	Intermediate Similarity	NPC474339
0.8155	Intermediate Similarity	NPC46998
0.8155	Intermediate Similarity	NPC133907
0.8155	Intermediate Similarity	NPC110443
0.8155	Intermediate Similarity	NPC164598
0.8125	Intermediate Similarity	NPC305475
0.8125	Intermediate Similarity	NPC475461
0.8119	Intermediate Similarity	NPC230800
0.8119	Intermediate Similarity	NPC473333
0.8119	Intermediate Similarity	NPC279621
0.81	Intermediate Similarity	NPC121825
0.81	Intermediate Similarity	NPC477131
0.8081	Intermediate Similarity	NPC470520
0.8081	Intermediate Similarity	NPC32494
0.8081	Intermediate Similarity	NPC175842
0.8073	Intermediate Similarity	NPC66108
0.8061	Intermediate Similarity	NPC225283
0.8039	Intermediate Similarity	NPC2666
0.8039	Intermediate Similarity	NPC471490
0.8021	Intermediate Similarity	NPC67081
0.8021	Intermediate Similarity	NPC165162
0.8021	Intermediate Similarity	NPC255307
0.8021	Intermediate Similarity	NPC471223
0.8021	Intermediate Similarity	NPC215364
0.802	Intermediate Similarity	NPC36954
0.802	Intermediate Similarity	NPC14961
0.802	Intermediate Similarity	NPC270013
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC476049
0.8	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC469645
0.8	Intermediate Similarity	NPC475945
0.8	Intermediate Similarity	NPC475871
0.8	Intermediate Similarity	NPC250315
0.8	Intermediate Similarity	NPC469692
0.8	Intermediate Similarity	NPC81419
0.7981	Intermediate Similarity	NPC150923
0.7981	Intermediate Similarity	NPC201718
0.798	Intermediate Similarity	NPC129419
0.798	Intermediate Similarity	NPC473448
0.7961	Intermediate Similarity	NPC473326
0.7961	Intermediate Similarity	NPC300584
0.7959	Intermediate Similarity	NPC202672
0.7941	Intermediate Similarity	NPC476315
0.7938	Intermediate Similarity	NPC284902
0.7938	Intermediate Similarity	NPC261721
0.7925	Intermediate Similarity	NPC100487
0.7921	Intermediate Similarity	NPC81386
0.7921	Intermediate Similarity	NPC470010
0.7921	Intermediate Similarity	NPC323008
0.7921	Intermediate Similarity	NPC470013
0.7921	Intermediate Similarity	NPC198853
0.7921	Intermediate Similarity	NPC474035
0.7921	Intermediate Similarity	NPC262133
0.7917	Intermediate Similarity	NPC141193
0.7917	Intermediate Similarity	NPC114979
0.7917	Intermediate Similarity	NPC96259
0.7917	Intermediate Similarity	NPC191476
0.7905	Intermediate Similarity	NPC324017
0.7905	Intermediate Similarity	NPC474747
0.7905	Intermediate Similarity	NPC320019
0.7905	Intermediate Similarity	NPC86077
0.7905	Intermediate Similarity	NPC471148
0.7905	Intermediate Similarity	NPC149371
0.79	Intermediate Similarity	NPC12172
0.79	Intermediate Similarity	NPC131209
0.79	Intermediate Similarity	NPC30515
0.79	Intermediate Similarity	NPC184463
0.79	Intermediate Similarity	NPC20713
0.79	Intermediate Similarity	NPC475925
0.79	Intermediate Similarity	NPC133698
0.79	Intermediate Similarity	NPC208886
0.7885	Intermediate Similarity	NPC288876
0.7879	Intermediate Similarity	NPC268298
0.7879	Intermediate Similarity	NPC473564
0.7879	Intermediate Similarity	NPC307092
0.7864	Intermediate Similarity	NPC161493
0.7857	Intermediate Similarity	NPC475703
0.7843	Intermediate Similarity	NPC471492
0.7843	Intermediate Similarity	NPC272050
0.7843	Intermediate Similarity	NPC67584
0.7843	Intermediate Similarity	NPC52044
0.7843	Intermediate Similarity	NPC170120
0.7843	Intermediate Similarity	NPC213698
0.7843	Intermediate Similarity	NPC474947
0.7822	Intermediate Similarity	NPC162205
0.7822	Intermediate Similarity	NPC212486
0.7822	Intermediate Similarity	NPC476300
0.7822	Intermediate Similarity	NPC295204
0.7822	Intermediate Similarity	NPC475302
0.7822	Intermediate Similarity	NPC273579
0.7822	Intermediate Similarity	NPC135776
0.7822	Intermediate Similarity	NPC288240
0.7812	Intermediate Similarity	NPC473390
0.7812	Intermediate Similarity	NPC40746
0.7812	Intermediate Similarity	NPC131669
0.7812	Intermediate Similarity	NPC169575
0.7812	Intermediate Similarity	NPC128429
0.781	Intermediate Similarity	NPC474742
0.781	Intermediate Similarity	NPC47880
0.781	Intermediate Similarity	NPC472753
0.781	Intermediate Similarity	NPC15993
0.781	Intermediate Similarity	NPC469851
0.78	Intermediate Similarity	NPC51004
0.78	Intermediate Similarity	NPC476004
0.78	Intermediate Similarity	NPC474761
0.78	Intermediate Similarity	NPC71533
0.78	Intermediate Similarity	NPC106510
0.78	Intermediate Similarity	NPC469718
0.78	Intermediate Similarity	NPC329857
0.7788	Intermediate Similarity	NPC471145
0.7788	Intermediate Similarity	NPC471144
0.7778	Intermediate Similarity	NPC469653
0.7778	Intermediate Similarity	NPC260343
0.7778	Intermediate Similarity	NPC471047
0.7778	Intermediate Similarity	NPC469628
0.7778	Intermediate Similarity	NPC469631
0.7778	Intermediate Similarity	NPC473658
0.7778	Intermediate Similarity	NPC477513
0.7778	Intermediate Similarity	NPC475906
0.7778	Intermediate Similarity	NPC475819
0.7778	Intermediate Similarity	NPC469853
0.7767	Intermediate Similarity	NPC213078
0.7767	Intermediate Similarity	NPC473291
0.7757	Intermediate Similarity	NPC472756
0.7757	Intermediate Similarity	NPC474741
0.7755	Intermediate Similarity	NPC50637
0.7755	Intermediate Similarity	NPC150755
0.7755	Intermediate Similarity	NPC122502
0.7755	Intermediate Similarity	NPC162071
0.7745	Intermediate Similarity	NPC140543
0.7745	Intermediate Similarity	NPC303942
0.7745	Intermediate Similarity	NPC473316
0.7745	Intermediate Similarity	NPC127019
0.7745	Intermediate Similarity	NPC190294
0.7745	Intermediate Similarity	NPC473330
0.7745	Intermediate Similarity	NPC57405
0.7736	Intermediate Similarity	NPC472754
0.7732	Intermediate Similarity	NPC476804
0.7723	Intermediate Similarity	NPC473321
0.7723	Intermediate Similarity	NPC261607
0.7723	Intermediate Similarity	NPC300312
0.7723	Intermediate Similarity	NPC111114
0.7714	Intermediate Similarity	NPC475053
0.7708	Intermediate Similarity	NPC229825
0.77	Intermediate Similarity	NPC166919
0.77	Intermediate Similarity	NPC307411
0.77	Intermediate Similarity	NPC474032
0.77	Intermediate Similarity	NPC64913
0.77	Intermediate Similarity	NPC212598
0.77	Intermediate Similarity	NPC242877
0.77	Intermediate Similarity	NPC51358
0.7685	Intermediate Similarity	NPC472751
0.7685	Intermediate Similarity	NPC469852
0.7685	Intermediate Similarity	NPC166115
0.7685	Intermediate Similarity	NPC472749
0.7685	Intermediate Similarity	NPC243998
0.7679	Intermediate Similarity	NPC469496
0.7679	Intermediate Similarity	NPC469454
0.7679	Intermediate Similarity	NPC469463
0.767	Intermediate Similarity	NPC471142
0.767	Intermediate Similarity	NPC473334
0.767	Intermediate Similarity	NPC107476
0.767	Intermediate Similarity	NPC471141
0.7664	Intermediate Similarity	NPC472747
0.7664	Intermediate Similarity	NPC472750
0.766	Intermediate Similarity	NPC93763
0.766	Intermediate Similarity	NPC108816
0.7658	Intermediate Similarity	NPC179798

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 NPC189609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1585
0.2-0.3	3568
0.3-0.4	2470
0.4-0.5	920
0.5-0.6	320
0.6-0.7	92
0.7-0.8	11
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
0.7615	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5282	Discontinued
0.7333	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7838	Discovery
0.7282	Intermediate Similarity	NPD46	Approved
0.7282	Intermediate Similarity	NPD6698	Approved
0.7257	Intermediate Similarity	NPD6371	Approved
0.7228	Intermediate Similarity	NPD4249	Approved
0.7188	Intermediate Similarity	NPD4756	Discovery
0.7184	Intermediate Similarity	NPD1695	Approved
0.7157	Intermediate Similarity	NPD4250	Approved
0.7157	Intermediate Similarity	NPD4251	Approved
0.713	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7154	Phase 3
0.7048	Intermediate Similarity	NPD7983	Approved
0.7043	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6053	Discontinued
0.6961	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5785	Approved
0.6822	Remote Similarity	NPD5779	Approved
0.6822	Remote Similarity	NPD5778	Approved
0.6796	Remote Similarity	NPD5363	Approved
0.6783	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6607	Remote Similarity	NPD6648	Approved
0.6602	Remote Similarity	NPD6110	Phase 1
0.6602	Remote Similarity	NPD5362	Discontinued
0.6549	Remote Similarity	NPD5344	Discontinued
0.6505	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4269	Approved
0.6505	Remote Similarity	NPD4270	Approved
0.6486	Remote Similarity	NPD7839	Suspended
0.6476	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD4821	Approved
0.6471	Remote Similarity	NPD4820	Approved
0.6471	Remote Similarity	NPD4819	Approved
0.6471	Remote Similarity	NPD4822	Approved
0.6471	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7640	Approved
0.646	Remote Similarity	NPD7639	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD5786	Approved
0.641	Remote Similarity	NPD5697	Approved
0.6408	Remote Similarity	NPD5369	Approved
0.64	Remote Similarity	NPD8515	Approved
0.64	Remote Similarity	NPD8516	Approved
0.64	Remote Similarity	NPD8517	Approved
0.64	Remote Similarity	NPD8513	Phase 3
0.6396	Remote Similarity	NPD5695	Phase 3
0.6387	Remote Similarity	NPD2067	Discontinued
0.6372	Remote Similarity	NPD7638	Approved
0.6372	Remote Similarity	NPD5696	Approved
0.6356	Remote Similarity	NPD7320	Approved
0.6356	Remote Similarity	NPD6881	Approved
0.6356	Remote Similarity	NPD6899	Approved
0.6346	Remote Similarity	NPD6435	Approved
0.6346	Remote Similarity	NPD5209	Approved
0.6343	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7115	Discovery
0.6336	Remote Similarity	NPD7260	Phase 2
0.6333	Remote Similarity	NPD6650	Approved
0.6333	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD5739	Approved
0.6325	Remote Similarity	NPD6402	Approved
0.6325	Remote Similarity	NPD7128	Approved
0.6325	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD4252	Approved
0.6303	Remote Similarity	NPD6012	Approved
0.6303	Remote Similarity	NPD6373	Approved
0.6303	Remote Similarity	NPD6013	Approved
0.6303	Remote Similarity	NPD6372	Approved
0.6303	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6014	Approved
0.6288	Remote Similarity	NPD6845	Suspended
0.6275	Remote Similarity	NPD4268	Approved
0.6275	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4271	Approved
0.6273	Remote Similarity	NPD7637	Suspended
0.6271	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7492	Approved
0.6239	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6101	Approved
0.6226	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6011	Approved
0.6202	Remote Similarity	NPD6616	Approved
0.6198	Remote Similarity	NPD8130	Phase 1
0.6198	Remote Similarity	NPD6847	Approved
0.6198	Remote Similarity	NPD6869	Approved
0.6198	Remote Similarity	NPD6617	Approved
0.619	Remote Similarity	NPD6054	Approved
0.619	Remote Similarity	NPD6319	Approved
0.6186	Remote Similarity	NPD6008	Approved
0.6154	Remote Similarity	NPD5368	Approved
0.6154	Remote Similarity	NPD7078	Approved
0.6154	Remote Similarity	NPD8074	Phase 3
0.6148	Remote Similarity	NPD8297	Approved
0.6148	Remote Similarity	NPD6882	Approved
0.6146	Remote Similarity	NPD3704	Approved
0.6142	Remote Similarity	NPD6016	Approved
0.6142	Remote Similarity	NPD6015	Approved
0.6136	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5331	Approved
0.6132	Remote Similarity	NPD5332	Approved
0.6126	Remote Similarity	NPD5693	Phase 1
0.6126	Remote Similarity	NPD6411	Approved
0.6111	Remote Similarity	NPD5279	Phase 3
0.6107	Remote Similarity	NPD7736	Approved
0.6098	Remote Similarity	NPD4632	Approved
0.6095	Remote Similarity	NPD4790	Discontinued
0.6094	Remote Similarity	NPD6370	Approved
0.6094	Remote Similarity	NPD5988	Approved
0.6094	Remote Similarity	NPD8080	Discontinued
0.608	Remote Similarity	NPD6009	Approved
0.6077	Remote Similarity	NPD7507	Approved
0.6075	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6399	Phase 3
0.6068	Remote Similarity	NPD5211	Phase 2
0.6063	Remote Similarity	NPD6059	Approved
0.6042	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5692	Phase 3
0.6032	Remote Similarity	NPD7641	Discontinued
0.6031	Remote Similarity	NPD8293	Discontinued
0.6019	Remote Similarity	NPD1696	Phase 3
0.6016	Remote Similarity	NPD5983	Phase 2
0.6016	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4695	Discontinued
0.5982	Remote Similarity	NPD5284	Approved
0.5982	Remote Similarity	NPD5694	Approved
0.5982	Remote Similarity	NPD5281	Approved
0.5982	Remote Similarity	NPD6050	Approved
0.5981	Remote Similarity	NPD6695	Phase 3
0.598	Remote Similarity	NPD8039	Approved
0.5966	Remote Similarity	NPD5141	Approved
0.5965	Remote Similarity	NPD5210	Approved
0.5965	Remote Similarity	NPD4629	Approved
0.5954	Remote Similarity	NPD8273	Phase 1
0.5952	Remote Similarity	NPD7500	Approved
0.595	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4753	Phase 2
0.5946	Remote Similarity	NPD5370	Suspended
0.594	Remote Similarity	NPD7319	Approved
0.5938	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD2204	Approved
0.5935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7632	Discontinued
0.5923	Remote Similarity	NPD7830	Approved
0.5923	Remote Similarity	NPD7642	Approved
0.5923	Remote Similarity	NPD7604	Phase 2
0.5923	Remote Similarity	NPD7829	Approved
0.5918	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5286	Approved
0.5897	Remote Similarity	NPD4696	Approved
0.5897	Remote Similarity	NPD5285	Approved
0.5893	Remote Similarity	NPD5207	Approved
0.5891	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6647	Phase 2
0.5868	Remote Similarity	NPD6412	Phase 2
0.5862	Remote Similarity	NPD7902	Approved
0.5862	Remote Similarity	NPD4755	Approved
0.5859	Remote Similarity	NPD7100	Approved
0.5859	Remote Similarity	NPD7101	Approved
0.5849	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8451	Approved
0.5833	Remote Similarity	NPD6336	Discontinued
0.5827	Remote Similarity	NPD7505	Discontinued
0.5827	Remote Similarity	NPD6317	Approved
0.5816	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6904	Approved
0.5804	Remote Similarity	NPD6080	Approved
0.5804	Remote Similarity	NPD6673	Approved
0.5802	Remote Similarity	NPD8328	Phase 3
0.5798	Remote Similarity	NPD5224	Approved
0.5798	Remote Similarity	NPD5225	Approved
0.5798	Remote Similarity	NPD5226	Approved
0.5798	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD8448	Approved
0.5781	Remote Similarity	NPD6335	Approved
0.5781	Remote Similarity	NPD6313	Approved
0.5781	Remote Similarity	NPD7327	Approved
0.5781	Remote Similarity	NPD7328	Approved
0.5781	Remote Similarity	NPD6314	Approved
0.5778	Remote Similarity	NPD5956	Approved
0.5769	Remote Similarity	NPD8444	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