NPASS Compound

Structure

NPC150978 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 -2.9312 1.5294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2596 -2.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -4.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9511 -1.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4467 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5547 0.6645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 0.6645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3456 -1.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 -3.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1132 -0.0861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9561 -0.0861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7237 -1.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1698 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0347 -1.4385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3773 -0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8996 -1.0220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5288 -2.8785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8098 -2.4705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3132 -1.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0347 -2.3985 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 2 9 2 0 0 0 0 3 10 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 8 1 1 6 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 17 1 1 0 0 0 12 7 1 1 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 15 17 1 6 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.13
Volume:	307.688
LogP:	1.076
LogD:	1.184
LogS:	-2.97
# Rotatable Bonds:	2
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.635
Fsp3:	0.588
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:	-4.629
MDCK Permeability:	2.2426151190302335e-05
Pgp-inhibitor:	0.734
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.571
20% Bioavailability (F20%):	0.459
30% Bioavailability (F30%):	0.874

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.907
Plasma Protein Binding (PPB):	67.89127349853516%
Volume Distribution (VD):	1.002
Pgp-substrate:	37.40217208862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.518
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	5.673
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.366
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.631
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.466
Carcinogencity:	0.663
Eye Corrosion:	0.91
Eye Irritation:	0.756
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC150978

Natural Product ID:	NPC150978
*Common Name:**	Angustibalin
IUPAC Name:	[(3aR,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
Synonyms:	6-O-Acetylhelenalin; Angustibalin
Standard InCHIKey:	DCNRYQODUSSOKC-HKHYKUHTSA-N
Standard InCHI:	InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12-,14-,15+,17+/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H]2[C@H](OC(=O)C2=C)C[C@H]([C@H]2[C@@]1(C)C(=O)C=C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486196
PubChem CID:	442142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene 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
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[16644542]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[16644542]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12107	Arnica montana	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
AC50	2
EC50	2
ED50	1
IC50	14
Others	1
Potency	43

Activity Type	# Activity
Cell Line	4
Individual Protein	35
NON-MOLECULAR	3
Organism	3
Others	16
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3728	Individual Protein	p53-binding protein Mdm-2	Homo sapiens	EC50	=	7680.0	nM	PMID[533952]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	3548.1	nM	PMID[533952]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	1000.0	nM	PMID[533952]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	3981.1	nM	PMID[533952]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	1258.9	nM	PMID[533952]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	44668.4	nM	PMID[533952]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	3162.3	nM	PMID[533952]
NPT538	Individual Protein	Niemann-Pick C1 protein	Homo sapiens	Potency	=	631.0	nM	PMID[533952]
NPT4358	Individual Protein	Type-1 angiotensin II receptor	Homo sapiens	IC50	=	21974.0	nM	PMID[533952]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	31622.8	nM	PMID[533952]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[533952]
NPT2892	Individual Protein	X-box-binding protein 1	Homo sapiens	IC50	=	2200.0	nM	PMID[533952]
NPT4120	Individual Protein	G-protein coupled receptor 55	Homo sapiens	IC50	=	4494.35	nM	PMID[533952]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[533952]
NPT2893	Individual Protein	DNA damage-inducible transcript 3 protein	Mus musculus	IC50	=	2480.0	nM	PMID[533952]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	5171.4	nM	PMID[533952]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[533952]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	990.0	nM	PMID[533952]
NPT1397	Cell Line	INS1	Rattus norvegicus	AC50	=	2132.0	nM	PMID[533952]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[533952]
NPT5114	Individual Protein	Beta-galactosidase	Escherichia coli	EC50	>	40000.0	nM	PMID[533952]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	707.9	nM	PMID[533952]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1158.2	nM	PMID[533952]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	1995.3	nM	PMID[533952]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	819.9	nM	PMID[533952]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[533952]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[533952]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	651.3	nM	PMID[533952]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	819.9	nM	PMID[533952]
NPT1283	Individual Protein	Paired box protein Pax-8	Homo sapiens	AC50	=	742.0	nM	PMID[533952]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[533952]
NPT168	Cell Line	P388	Mus musculus	T/C	=	78.0	%	PMID[533954]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	220.0	nM	PMID[533950]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1300.0	nM	PMID[533950]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	15848.9	nM	PMID[533952]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	1309.2	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	=	6513.1	nM	PMID[533952]
NPT2	Others	Unspecified		IC50	=	2066.0	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	9200.0	nM	PMID[533952]
NPT2	Others	Unspecified		IC50	>	80000.0	nM	PMID[533952]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2936.2	nM	PMID[533952]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	56234.1	nM	PMID[533952]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[533952]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	354.8	nM	PMID[533952]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2078.7	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	1584.9	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	1412.5	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	2238.7	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	4610.9	nM	PMID[533952]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[533952]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	706.32	nM	PMID[533953]
NPT27	Others	Unspecified		IC50	=	7340.0	nM	PMID[533953]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	710.0	nM	PMID[533953]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[533952]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[533952]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.29	ug ml-1	PMID[533954]
NPT2	Others	Unspecified		Potency	n.a.	3162.3	nM	PMID[533952]

☑ 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 NPC150978 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	234
0.1-0.2	1450
0.2-0.3	5748
0.3-0.4	12098
0.4-0.5	12025
0.5-0.6	6732
0.6-0.7	3562
0.7-0.8	742
0.8-0.85	66
0.85-0.9	19
0.9-0.95	15
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC123177
1.0	High Similarity	NPC70595
1.0	High Similarity	NPC74103
0.9882	High Similarity	NPC253144
0.9767	High Similarity	NPC284185
0.9444	High Similarity	NPC169205
0.9438	High Similarity	NPC48803
0.9438	High Similarity	NPC90121
0.9438	High Similarity	NPC275960
0.9438	High Similarity	NPC193645
0.9412	High Similarity	NPC70422
0.9412	High Similarity	NPC104961
0.9412	High Similarity	NPC70555
0.9341	High Similarity	NPC54843
0.9341	High Similarity	NPC141191
0.9333	High Similarity	NPC185553
0.9294	High Similarity	NPC21471
0.9294	High Similarity	NPC33570
0.9294	High Similarity	NPC161957
0.9059	High Similarity	NPC39588
0.8966	High Similarity	NPC238593
0.8901	High Similarity	NPC167219
0.8876	High Similarity	NPC52198
0.8876	High Similarity	NPC117405
0.8854	High Similarity	NPC203659
0.8842	High Similarity	NPC225353
0.8837	High Similarity	NPC215294
0.875	High Similarity	NPC107787
0.875	High Similarity	NPC110989
0.8736	High Similarity	NPC115786
0.8706	High Similarity	NPC223904
0.8696	High Similarity	NPC289004
0.8681	High Similarity	NPC111114
0.8681	High Similarity	NPC261607
0.8681	High Similarity	NPC300312
0.8636	High Similarity	NPC78089
0.8621	High Similarity	NPC54468
0.8488	Intermediate Similarity	NPC69271
0.8488	Intermediate Similarity	NPC74673
0.8478	Intermediate Similarity	NPC286341
0.8478	Intermediate Similarity	NPC191339
0.8462	Intermediate Similarity	NPC12872
0.8462	Intermediate Similarity	NPC168679
0.8391	Intermediate Similarity	NPC35089
0.8391	Intermediate Similarity	NPC281949
0.8391	Intermediate Similarity	NPC39411
0.8391	Intermediate Similarity	NPC10276
0.8391	Intermediate Similarity	NPC255580
0.8391	Intermediate Similarity	NPC25684
0.8391	Intermediate Similarity	NPC301477
0.837	Intermediate Similarity	NPC62815
0.8351	Intermediate Similarity	NPC171759
0.8276	Intermediate Similarity	NPC302426
0.8276	Intermediate Similarity	NPC293418
0.8276	Intermediate Similarity	NPC290508
0.8276	Intermediate Similarity	NPC73052
0.8276	Intermediate Similarity	NPC6823
0.8276	Intermediate Similarity	NPC276356
0.8265	Intermediate Similarity	NPC474747
0.8229	Intermediate Similarity	NPC213947
0.8229	Intermediate Similarity	NPC108475
0.8229	Intermediate Similarity	NPC170143
0.8211	Intermediate Similarity	NPC304886
0.8191	Intermediate Similarity	NPC135776
0.8182	Intermediate Similarity	NPC475945
0.8182	Intermediate Similarity	NPC475871
0.8172	Intermediate Similarity	NPC129419
0.8163	Intermediate Similarity	NPC474742
0.8163	Intermediate Similarity	NPC477950
0.8152	Intermediate Similarity	NPC475906
0.8152	Intermediate Similarity	NPC469628
0.8152	Intermediate Similarity	NPC469631
0.8152	Intermediate Similarity	NPC469653
0.8152	Intermediate Similarity	NPC471047
0.814	Intermediate Similarity	NPC476794
0.814	Intermediate Similarity	NPC470240
0.8125	Intermediate Similarity	NPC142529
0.8125	Intermediate Similarity	NPC91771
0.8105	Intermediate Similarity	NPC140543
0.8105	Intermediate Similarity	NPC477131
0.8105	Intermediate Similarity	NPC476267
0.81	Intermediate Similarity	NPC474741
0.809	Intermediate Similarity	NPC173609
0.8085	Intermediate Similarity	NPC133698
0.8065	Intermediate Similarity	NPC268298
0.8043	Intermediate Similarity	NPC478144
0.8043	Intermediate Similarity	NPC201658
0.8021	Intermediate Similarity	NPC474490
0.8	Intermediate Similarity	NPC473234
0.8	Intermediate Similarity	NPC60386
0.8	Intermediate Similarity	NPC318468
0.8	Intermediate Similarity	NPC473263
0.8	Intermediate Similarity	NPC473273
0.8	Intermediate Similarity	NPC475873
0.8	Intermediate Similarity	NPC153590
0.8	Intermediate Similarity	NPC475947
0.8	Intermediate Similarity	NPC308656
0.7978	Intermediate Similarity	NPC471325
0.7978	Intermediate Similarity	NPC141810
0.7957	Intermediate Similarity	NPC475902
0.7955	Intermediate Similarity	NPC63649
0.7955	Intermediate Similarity	NPC270126
0.7955	Intermediate Similarity	NPC469620
0.7955	Intermediate Similarity	NPC182550
0.7955	Intermediate Similarity	NPC617
0.7955	Intermediate Similarity	NPC469690
0.7955	Intermediate Similarity	NPC264227
0.7955	Intermediate Similarity	NPC178277
0.7955	Intermediate Similarity	NPC472965
0.7938	Intermediate Similarity	NPC126156
0.7935	Intermediate Similarity	NPC284902
0.7935	Intermediate Similarity	NPC309757
0.7935	Intermediate Similarity	NPC304558
0.7935	Intermediate Similarity	NPC236692
0.7935	Intermediate Similarity	NPC64153
0.7931	Intermediate Similarity	NPC195785
0.7931	Intermediate Similarity	NPC65603
0.7931	Intermediate Similarity	NPC208223
0.7931	Intermediate Similarity	NPC15975
0.7921	Intermediate Similarity	NPC309190
0.7921	Intermediate Similarity	NPC100487
0.7917	Intermediate Similarity	NPC198853
0.7917	Intermediate Similarity	NPC148463
0.7912	Intermediate Similarity	NPC165287
0.7907	Intermediate Similarity	NPC138408
0.7907	Intermediate Similarity	NPC226669
0.7907	Intermediate Similarity	NPC193351
0.7895	Intermediate Similarity	NPC20713
0.7895	Intermediate Similarity	NPC221282
0.7895	Intermediate Similarity	NPC131209
0.7872	Intermediate Similarity	NPC166919
0.7872	Intermediate Similarity	NPC32922
0.7872	Intermediate Similarity	NPC4986
0.7849	Intermediate Similarity	NPC24728
0.7849	Intermediate Similarity	NPC72513
0.7849	Intermediate Similarity	NPC475703
0.7849	Intermediate Similarity	NPC237540
0.7849	Intermediate Similarity	NPC478145
0.7843	Intermediate Similarity	NPC291643
0.7841	Intermediate Similarity	NPC472960
0.7841	Intermediate Similarity	NPC128276
0.783	Intermediate Similarity	NPC209058
0.7826	Intermediate Similarity	NPC125290
0.7826	Intermediate Similarity	NPC165162
0.7826	Intermediate Similarity	NPC110405
0.7826	Intermediate Similarity	NPC155873
0.7816	Intermediate Similarity	NPC123360
0.7812	Intermediate Similarity	NPC475302
0.7812	Intermediate Similarity	NPC200237
0.7802	Intermediate Similarity	NPC272814
0.7802	Intermediate Similarity	NPC474703
0.78	Intermediate Similarity	NPC128733
0.78	Intermediate Similarity	NPC185141
0.78	Intermediate Similarity	NPC110443
0.78	Intermediate Similarity	NPC46998
0.78	Intermediate Similarity	NPC472753
0.78	Intermediate Similarity	NPC47880
0.78	Intermediate Similarity	NPC133907
0.7791	Intermediate Similarity	NPC476355
0.7789	Intermediate Similarity	NPC152467
0.7789	Intermediate Similarity	NPC71533
0.7789	Intermediate Similarity	NPC469368
0.7789	Intermediate Similarity	NPC106510
0.7789	Intermediate Similarity	NPC312042
0.7778	Intermediate Similarity	NPC47635
0.7778	Intermediate Similarity	NPC208233
0.7778	Intermediate Similarity	NPC42470
0.7766	Intermediate Similarity	NPC226863
0.7766	Intermediate Similarity	NPC215831
0.7766	Intermediate Similarity	NPC471149
0.7766	Intermediate Similarity	NPC476805
0.7755	Intermediate Similarity	NPC18019
0.7755	Intermediate Similarity	NPC24956
0.7755	Intermediate Similarity	NPC476275
0.7742	Intermediate Similarity	NPC150755
0.7742	Intermediate Similarity	NPC475461
0.7742	Intermediate Similarity	NPC38576
0.7742	Intermediate Similarity	NPC305475
0.7742	Intermediate Similarity	NPC279859
0.7732	Intermediate Similarity	NPC473316
0.7732	Intermediate Similarity	NPC323008
0.7732	Intermediate Similarity	NPC470010
0.7732	Intermediate Similarity	NPC477130
0.7732	Intermediate Similarity	NPC262133
0.7732	Intermediate Similarity	NPC473330
0.7732	Intermediate Similarity	NPC469632
0.7732	Intermediate Similarity	NPC473331
0.7732	Intermediate Similarity	NPC470013
0.7732	Intermediate Similarity	NPC477129
0.7732	Intermediate Similarity	NPC470697
0.7727	Intermediate Similarity	NPC141789
0.7727	Intermediate Similarity	NPC57744
0.7727	Intermediate Similarity	NPC122264
0.7727	Intermediate Similarity	NPC97516
0.7727	Intermediate Similarity	NPC474760
0.7727	Intermediate Similarity	NPC476028
0.7727	Intermediate Similarity	NPC171204
0.7723	Intermediate Similarity	NPC149371
0.7723	Intermediate Similarity	NPC472754
0.7717	Intermediate Similarity	NPC38569

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 NPC150978 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	1987
0.2-0.3	3954
0.3-0.4	2029
0.4-0.5	621
0.5-0.6	256
0.6-0.7	87
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9438	High Similarity	NPD1698	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1695	Approved
0.7692	Intermediate Similarity	NPD5209	Approved
0.7634	Intermediate Similarity	NPD1694	Approved
0.7604	Intermediate Similarity	NPD5785	Approved
0.7596	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5282	Discontinued
0.7547	Intermediate Similarity	NPD6371	Approved
0.7312	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD5363	Approved
0.701	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6947	Remote Similarity	NPD6435	Approved
0.6852	Remote Similarity	NPD6008	Approved
0.6842	Remote Similarity	NPD5369	Approved
0.68	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4269	Approved
0.6771	Remote Similarity	NPD4270	Approved
0.6765	Remote Similarity	NPD5779	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6737	Remote Similarity	NPD5368	Approved
0.6701	Remote Similarity	NPD7154	Phase 3
0.6701	Remote Similarity	NPD5362	Discontinued
0.67	Remote Similarity	NPD6903	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6602	Remote Similarity	NPD6399	Phase 3
0.66	Remote Similarity	NPD3573	Approved
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD6698	Approved
0.6569	Remote Similarity	NPD5207	Approved
0.6569	Remote Similarity	NPD46	Approved
0.6562	Remote Similarity	NPD4252	Approved
0.6559	Remote Similarity	NPD8039	Approved
0.6549	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6649	Approved
0.6538	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7900	Approved
0.6535	Remote Similarity	NPD5737	Approved
0.6535	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6672	Approved
0.6526	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6014	Approved
0.6518	Remote Similarity	NPD6013	Approved
0.6518	Remote Similarity	NPD6012	Approved
0.6505	Remote Similarity	NPD5693	Phase 1
0.6491	Remote Similarity	NPD6053	Discontinued
0.6476	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD6686	Approved
0.6408	Remote Similarity	NPD7838	Discovery
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6869	Approved
0.6404	Remote Similarity	NPD6617	Approved
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6392	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD7902	Approved
0.6348	Remote Similarity	NPD8297	Approved
0.6348	Remote Similarity	NPD6882	Approved
0.6339	Remote Similarity	NPD5701	Approved
0.6337	Remote Similarity	NPD4249	Approved
0.6321	Remote Similarity	NPD5695	Phase 3
0.6311	Remote Similarity	NPD7492	Approved
0.6296	Remote Similarity	NPD5696	Approved
0.6292	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4250	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.6273	Remote Similarity	NPD5211	Phase 2
0.6262	Remote Similarity	NPD7839	Suspended
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD5285	Approved
0.6239	Remote Similarity	NPD5286	Approved
0.6226	Remote Similarity	NPD7748	Approved
0.6226	Remote Similarity	NPD6001	Approved
0.6224	Remote Similarity	NPD4822	Approved
0.6224	Remote Similarity	NPD4820	Approved
0.6224	Remote Similarity	NPD4821	Approved
0.6224	Remote Similarity	NPD4819	Approved
0.621	Remote Similarity	NPD7078	Approved
0.6204	Remote Similarity	NPD6083	Phase 2
0.6204	Remote Similarity	NPD6084	Phase 2
0.6198	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6016	Approved
0.6198	Remote Similarity	NPD6015	Approved
0.619	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD5284	Approved
0.619	Remote Similarity	NPD5694	Approved
0.619	Remote Similarity	NPD5281	Approved
0.619	Remote Similarity	NPD6079	Approved
0.6186	Remote Similarity	NPD4268	Approved
0.6186	Remote Similarity	NPD4271	Approved
0.6161	Remote Similarity	NPD5141	Approved
0.616	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD6904	Approved
0.6154	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD6080	Approved
0.6148	Remote Similarity	NPD5988	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.6147	Remote Similarity	NPD7638	Approved
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5224	Approved
0.6126	Remote Similarity	NPD4633	Approved
0.6126	Remote Similarity	NPD5226	Approved
0.6126	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5222	Approved
0.6111	Remote Similarity	NPD5221	Approved
0.61	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5692	Phase 3
0.6091	Remote Similarity	NPD7639	Approved
0.6091	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD229	Approved
0.6071	Remote Similarity	NPD5175	Approved
0.6071	Remote Similarity	NPD5174	Approved
0.6066	Remote Similarity	NPD8513	Phase 3
0.6066	Remote Similarity	NPD8517	Approved
0.6066	Remote Similarity	NPD8515	Approved
0.6066	Remote Similarity	NPD8516	Approved
0.6061	Remote Similarity	NPD4695	Discontinued
0.6058	Remote Similarity	NPD5208	Approved
0.6055	Remote Similarity	NPD5173	Approved
0.6055	Remote Similarity	NPD4755	Approved
0.6053	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6274	Approved
0.604	Remote Similarity	NPD5332	Approved
0.604	Remote Similarity	NPD5331	Approved
0.6038	Remote Similarity	NPD6050	Approved
0.6038	Remote Similarity	NPD7515	Phase 2
0.6036	Remote Similarity	NPD5223	Approved
0.6034	Remote Similarity	NPD4634	Approved
0.6033	Remote Similarity	NPD7100	Approved
0.6033	Remote Similarity	NPD7101	Approved
0.6019	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD3618	Phase 1
0.6019	Remote Similarity	NPD5210	Approved
0.6017	Remote Similarity	NPD4632	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD6059	Approved
0.5984	Remote Similarity	NPD7319	Approved
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3668	Phase 3
0.598	Remote Similarity	NPD3665	Phase 1
0.598	Remote Similarity	NPD3133	Approved
0.598	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3666	Approved
0.5963	Remote Similarity	NPD4697	Phase 3
0.5952	Remote Similarity	NPD8293	Discontinued
0.595	Remote Similarity	NPD6313	Approved
0.595	Remote Similarity	NPD6314	Approved
0.595	Remote Similarity	NPD6335	Approved
0.5946	Remote Similarity	NPD6648	Approved
0.5946	Remote Similarity	NPD4700	Approved
0.5941	Remote Similarity	NPD3667	Approved
0.5929	Remote Similarity	NPD6052	Approved
0.5917	Remote Similarity	NPD6868	Approved
0.5897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5344	Discontinued
0.5888	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7507	Approved
0.587	Remote Similarity	NPD7331	Phase 2
0.5868	Remote Similarity	NPD6009	Approved
0.5865	Remote Similarity	NPD6098	Approved
0.5865	Remote Similarity	NPD4519	Discontinued
0.5865	Remote Similarity	NPD5279	Phase 3
0.5865	Remote Similarity	NPD4623	Approved
0.5865	Remote Similarity	NPD6422	Discontinued
0.5862	Remote Similarity	NPD4730	Approved
0.5862	Remote Similarity	NPD4729	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