NPASS Compound

Structure

CID241847 OpenBabel06191716042D 46 52 0 0 1 0 0 0 0 0999 V2000 -1.5777 -5.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 1.4148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0842 -2.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3330 -5.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4396 0.4334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2454 -0.0509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6174 -0.0222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1966 -5.6585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0133 -5.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3897 -5.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8004 0.4811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2838 -2.7443 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2289 -0.9908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6008 -0.9622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0175 -4.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3939 -4.2502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4066 -1.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2050 -3.7894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2092 -2.8599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0260 -2.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6173 0.0284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3002 -3.6780 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0302 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6337 -0.9053 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6829 -3.7064 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4024 -2.3810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4998 -4.1591 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8333 -1.3864 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5926 -3.7821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8272 -2.8672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6665 -2.7727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0164 -0.9337 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4177 0.5095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1170 -4.1306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8423 -0.9913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4505 -1.3579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8825 -4.1875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7806 -4.2446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6393 -2.4047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5162 -5.0928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4669 -2.2916 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 -4.8231 -3.7967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7840 -1.4148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5968 -2.8526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -2.3201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 4 40 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 2 1 6 0 0 0 11 21 1 0 0 0 0 11 42 1 0 0 0 0 12 3 1 6 0 0 0 12 22 1 0 0 0 0 12 41 1 0 0 0 0 13 17 1 0 0 0 0 13 23 2 0 0 0 0 14 17 1 0 0 0 0 14 44 1 0 0 0 0 15 18 2 0 0 0 0 15 43 1 0 0 0 0 16 18 1 0 0 0 0 16 29 1 0 0 0 0 17 26 2 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 30 1 0 0 0 0 21 24 1 0 0 0 0 21 33 1 6 0 0 0 22 27 1 0 0 0 0 22 34 1 6 0 0 0 23 35 1 0 0 0 0 24 28 1 0 0 0 0 24 36 1 6 0 0 0 25 27 1 0 0 0 0 25 31 1 0 0 0 0 25 37 1 1 0 0 0 26 45 1 0 0 0 0 27 40 1 6 0 0 0 28 32 1 0 0 0 0 28 46 1 1 0 0 0 29 38 2 0 0 0 0 29 45 1 0 0 0 0 30 39 2 0 0 0 0 30 43 1 0 0 0 0 31 41 1 0 0 0 0 31 46 1 1 0 0 0 32 42 1 0 0 0 0 32 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	640.18
Volume:	598.831
LogP:	2.93
LogD:	2.132
LogS:	-5.643
# Rotatable Bonds:	5
TPSA:	207.72
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	5.076
Fsp3:	0.438
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.143
MDCK Permeability:	2.9549331884481944e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.576
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	71.4903793334961%
Volume Distribution (VD):	0.667
Pgp-substrate:	17.165935516357422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.131
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	0.79
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.947
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.578
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.795
Carcinogencity:	0.438
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC241847

Natural Product ID:	NPC241847
*Common Name:**	Chartreusin
IUPAC Name:	n.a.
Synonyms:	Chartreusin
Standard InCHIKey:	PONPPNYZKHNPKZ-RYBWXQSLSA-N
Standard InCHI:	InChI=1S/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3/t11-,12-,21+,22+,24+,25-,27+,28-,31-,32+/m1/s1
SMILES:	CO[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@@H](O[C@@H]([C@@H]([C@@H]2O)O)C)Oc2cccc3c2c2oc(=O)c4c5c2c(c3O)c(=O)oc5ccc4C)O[C@@H]([C@@H]1O)C
Synthetic Gene Cluster:	BGC0000207;
ChEMBL Identifier:	CHEMBL1554674
PubChem CID:	5281394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones [CHEMONTID:0001646] Naphthopyranone glycosides

*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
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7950	Cortinellus shiitake	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4212	Acia weinmanni	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6069	Leontice thalictroides	Species	Berberidaceae	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
Others	3
Potency	10

Activity Type	# Activity
CELL-LINE	1
Individual Protein	11
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[546550]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	35481.3	nM	PMID[546550]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	7062.7	nM	PMID[546550]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	11220.2	nM	PMID[546550]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[546550]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[546550]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[546550]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	17.54	%	PMID[546551]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	28183.8	nM	PMID[546550]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[546550]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[546550]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	7.94	%	PMID[546551]
NPT22036	CELL-LINE	HL	Homo sapiens	Activity	=	4.0	%	PMID[546552]

☑ 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 NPC241847 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	448
0.1-0.2	1934
0.2-0.3	3964
0.3-0.4	9306
0.4-0.5	8721
0.5-0.6	5660
0.6-0.7	5877
0.7-0.8	5620
0.8-0.85	905
0.85-0.9	243
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC245059
0.9419	High Similarity	NPC84494
0.9364	High Similarity	NPC164047
0.9364	High Similarity	NPC470448
0.9364	High Similarity	NPC470453
0.9364	High Similarity	NPC470452
0.9306	High Similarity	NPC58538
0.9257	High Similarity	NPC224557
0.9257	High Similarity	NPC292706
0.9253	High Similarity	NPC477860
0.9253	High Similarity	NPC475161
0.9244	High Similarity	NPC63105
0.9244	High Similarity	NPC199533
0.9244	High Similarity	NPC470454
0.9205	High Similarity	NPC87583
0.9191	High Similarity	NPC289876
0.9191	High Similarity	NPC102053
0.9181	High Similarity	NPC313304
0.9172	High Similarity	NPC99216
0.9143	High Similarity	NPC197357
0.9143	High Similarity	NPC85316
0.9121	High Similarity	NPC131405
0.9112	High Similarity	NPC17432
0.9096	High Similarity	NPC475220
0.9096	High Similarity	NPC473686
0.9096	High Similarity	NPC221140
0.9096	High Similarity	NPC475352
0.9096	High Similarity	NPC229817
0.9091	High Similarity	NPC293227
0.9091	High Similarity	NPC473631
0.9091	High Similarity	NPC473717
0.9091	High Similarity	NPC475662
0.9086	High Similarity	NPC299149
0.9086	High Similarity	NPC114257
0.9086	High Similarity	NPC277710
0.9086	High Similarity	NPC153578
0.908	High Similarity	NPC46958
0.908	High Similarity	NPC475246
0.9075	High Similarity	NPC213052
0.9075	High Similarity	NPC85368
0.9075	High Similarity	NPC203751
0.907	High Similarity	NPC298778
0.9064	High Similarity	NPC249977
0.9061	High Similarity	NPC470198
0.9061	High Similarity	NPC470195
0.9061	High Similarity	NPC470197
0.9061	High Similarity	NPC282474
0.9061	High Similarity	NPC470200
0.9061	High Similarity	NPC314687
0.9061	High Similarity	NPC470193
0.9061	High Similarity	NPC470194
0.9061	High Similarity	NPC470196
0.9061	High Similarity	NPC316274
0.9023	High Similarity	NPC3718
0.9023	High Similarity	NPC68381
0.9017	High Similarity	NPC288152
0.9017	High Similarity	NPC315619
0.9017	High Similarity	NPC9002
0.9017	High Similarity	NPC257011
0.9017	High Similarity	NPC137871
0.9	High Similarity	NPC264302
0.8971	High Similarity	NPC314489
0.8971	High Similarity	NPC198893
0.8971	High Similarity	NPC232818
0.896	High Similarity	NPC199079
0.896	High Similarity	NPC210808
0.895	High Similarity	NPC470199
0.895	High Similarity	NPC314459
0.8947	High Similarity	NPC7752
0.8944	High Similarity	NPC314672
0.8941	High Similarity	NPC216752
0.8939	High Similarity	NPC105591
0.8935	High Similarity	NPC328093
0.8914	High Similarity	NPC474345
0.8914	High Similarity	NPC470667
0.8908	High Similarity	NPC271385
0.8908	High Similarity	NPC30432
0.8908	High Similarity	NPC76128
0.8908	High Similarity	NPC5029
0.8908	High Similarity	NPC111536
0.8902	High Similarity	NPC246274
0.8902	High Similarity	NPC259905
0.8901	High Similarity	NPC477082
0.8895	High Similarity	NPC178851
0.8895	High Similarity	NPC48474
0.8895	High Similarity	NPC70441
0.8889	High Similarity	NPC477081
0.8889	High Similarity	NPC477083
0.8889	High Similarity	NPC473618
0.8876	High Similarity	NPC476203
0.8864	High Similarity	NPC92403
0.8864	High Similarity	NPC66820
0.8864	High Similarity	NPC170018
0.8864	High Similarity	NPC76112
0.8857	High Similarity	NPC168789
0.8851	High Similarity	NPC76047
0.8851	High Similarity	NPC52598
0.884	High Similarity	NPC31208
0.884	High Similarity	NPC93065
0.884	High Similarity	NPC469652
0.884	High Similarity	NPC472720
0.884	High Similarity	NPC187632
0.884	High Similarity	NPC472724
0.884	High Similarity	NPC160543
0.884	High Similarity	NPC472721
0.8837	High Similarity	NPC178281
0.8833	High Similarity	NPC179947
0.882	High Similarity	NPC53680
0.882	High Similarity	NPC208797
0.8814	High Similarity	NPC472387
0.8811	High Similarity	NPC174140
0.8807	High Similarity	NPC186800
0.8807	High Similarity	NPC307754
0.8807	High Similarity	NPC223735
0.8793	High Similarity	NPC222455
0.8785	High Similarity	NPC290289
0.8785	High Similarity	NPC223534
0.8785	High Similarity	NPC240200
0.8785	High Similarity	NPC158214
0.8785	High Similarity	NPC205721
0.8778	High Similarity	NPC261623
0.8778	High Similarity	NPC111490
0.8771	High Similarity	NPC321916
0.8764	High Similarity	NPC161609
0.8764	High Similarity	NPC275690
0.8757	High Similarity	NPC67629
0.8757	High Similarity	NPC79736
0.8757	High Similarity	NPC475233
0.875	High Similarity	NPC199357
0.875	High Similarity	NPC472054
0.8743	High Similarity	NPC241874
0.8736	High Similarity	NPC63470
0.8736	High Similarity	NPC298847
0.8729	High Similarity	NPC469649
0.8729	High Similarity	NPC65489
0.8729	High Similarity	NPC260521
0.8722	High Similarity	NPC75574
0.8722	High Similarity	NPC49690
0.8722	High Similarity	NPC318119
0.8722	High Similarity	NPC231254
0.8721	High Similarity	NPC146837
0.8721	High Similarity	NPC101116
0.8721	High Similarity	NPC278329
0.8721	High Similarity	NPC212099
0.8721	High Similarity	NPC190450
0.8708	High Similarity	NPC267549
0.8708	High Similarity	NPC476620
0.8708	High Similarity	NPC476619
0.8708	High Similarity	NPC476621
0.8708	High Similarity	NPC476623
0.8708	High Similarity	NPC476622
0.8708	High Similarity	NPC476618
0.8706	High Similarity	NPC177742
0.8701	High Similarity	NPC102028
0.8693	High Similarity	NPC267254
0.8693	High Similarity	NPC301683
0.8693	High Similarity	NPC472386
0.8693	High Similarity	NPC183441
0.8689	High Similarity	NPC321046
0.8689	High Similarity	NPC97924
0.8689	High Similarity	NPC40078
0.8689	High Similarity	NPC471091
0.8686	High Similarity	NPC473202
0.8678	High Similarity	NPC68592
0.8678	High Similarity	NPC262222
0.8678	High Similarity	NPC298666
0.8674	High Similarity	NPC469650
0.8671	High Similarity	NPC124155
0.8671	High Similarity	NPC257566
0.8667	High Similarity	NPC129533
0.8667	High Similarity	NPC123259
0.8663	High Similarity	NPC132737
0.8663	High Similarity	NPC73148
0.8659	High Similarity	NPC212290
0.8655	High Similarity	NPC53139
0.8652	High Similarity	NPC176246
0.8652	High Similarity	NPC297574
0.8652	High Similarity	NPC324220
0.8652	High Similarity	NPC312630
0.8644	High Similarity	NPC219600
0.8644	High Similarity	NPC236191
0.8644	High Similarity	NPC98776
0.8644	High Similarity	NPC239549
0.8644	High Similarity	NPC166674
0.8644	High Similarity	NPC34436
0.8644	High Similarity	NPC263119
0.8644	High Similarity	NPC46640
0.8644	High Similarity	NPC51774
0.8639	High Similarity	NPC185103
0.8636	High Similarity	NPC477572
0.8636	High Similarity	NPC293004
0.8636	High Similarity	NPC251144
0.8636	High Similarity	NPC477573
0.8636	High Similarity	NPC241387
0.8636	High Similarity	NPC477571
0.8619	High Similarity	NPC114120
0.8619	High Similarity	NPC167045
0.8613	High Similarity	NPC44947
0.8613	High Similarity	NPC97637
0.8613	High Similarity	NPC187934

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 NPC241847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	988
0.2-0.3	1958
0.3-0.4	2739
0.4-0.5	1905
0.5-0.6	786
0.6-0.7	240
0.7-0.8	106
0.8-0.85	16
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9037	High Similarity	NPD7782	Clinical (unspecified phase)
0.9037	High Similarity	NPD7783	Phase 2
0.8864	High Similarity	NPD8313	Approved
0.8864	High Similarity	NPD8312	Approved
0.8833	High Similarity	NPD7879	Clinical (unspecified phase)
0.8619	High Similarity	NPD8397	Clinical (unspecified phase)
0.858	High Similarity	NPD5844	Phase 1
0.858	High Similarity	NPD7804	Clinical (unspecified phase)
0.8531	High Similarity	NPD7074	Phase 3
0.8448	Intermediate Similarity	NPD6959	Discontinued
0.8436	Intermediate Similarity	NPD6559	Discontinued
0.8371	Intermediate Similarity	NPD7054	Approved
0.8342	Intermediate Similarity	NPD8151	Discontinued
0.8324	Intermediate Similarity	NPD7472	Approved
0.8314	Intermediate Similarity	NPD8455	Phase 2
0.8295	Intermediate Similarity	NPD6232	Discontinued
0.8287	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8287	Intermediate Similarity	NPD7808	Phase 3
0.8276	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7435	Discontinued
0.8258	Intermediate Similarity	NPD7473	Discontinued
0.8232	Intermediate Similarity	NPD7251	Discontinued
0.8208	Intermediate Similarity	NPD7819	Suspended
0.8177	Intermediate Similarity	NPD6797	Phase 2
0.8177	Intermediate Similarity	NPD7698	Approved
0.8177	Intermediate Similarity	NPD7697	Approved
0.8177	Intermediate Similarity	NPD7696	Phase 3
0.8135	Intermediate Similarity	NPD7870	Phase 2
0.8135	Intermediate Similarity	NPD7871	Phase 2
0.8115	Intermediate Similarity	NPD6782	Approved
0.8115	Intermediate Similarity	NPD6780	Approved
0.8115	Intermediate Similarity	NPD6776	Approved
0.8115	Intermediate Similarity	NPD6777	Approved
0.8115	Intermediate Similarity	NPD6781	Approved
0.8115	Intermediate Similarity	NPD6778	Approved
0.8115	Intermediate Similarity	NPD6779	Approved
0.8112	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD7874	Approved
0.8103	Intermediate Similarity	NPD7701	Phase 2
0.8101	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6166	Phase 2
0.8068	Intermediate Similarity	NPD7075	Discontinued
0.8057	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD3818	Discontinued
0.8011	Intermediate Similarity	NPD7228	Approved
0.8011	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD7699	Phase 2
0.801	Intermediate Similarity	NPD7700	Phase 2
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD8320	Phase 1
0.7949	Intermediate Similarity	NPD8319	Approved
0.7938	Intermediate Similarity	NPD6823	Phase 2
0.7931	Intermediate Similarity	NPD4380	Phase 2
0.7914	Intermediate Similarity	NPD8150	Discontinued
0.791	Intermediate Similarity	NPD7768	Phase 2
0.7898	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7801	Approved
0.7886	Intermediate Similarity	NPD7411	Suspended
0.788	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD3226	Approved
0.7853	Intermediate Similarity	NPD6534	Approved
0.7853	Intermediate Similarity	NPD6535	Approved
0.7814	Intermediate Similarity	NPD3751	Discontinued
0.7805	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD1465	Phase 2
0.779	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD5494	Approved
0.7771	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3749	Approved
0.7753	Intermediate Similarity	NPD5402	Approved
0.7746	Intermediate Similarity	NPD2533	Approved
0.7746	Intermediate Similarity	NPD2532	Approved
0.7746	Intermediate Similarity	NPD2534	Approved
0.774	Intermediate Similarity	NPD1934	Approved
0.774	Intermediate Similarity	NPD6801	Discontinued
0.7708	Intermediate Similarity	NPD6212	Phase 3
0.7708	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6213	Phase 3
0.7697	Intermediate Similarity	NPD2801	Approved
0.7672	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7458	Discontinued
0.7647	Intermediate Similarity	NPD7240	Approved
0.7644	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD37	Approved
0.7637	Intermediate Similarity	NPD7199	Phase 2
0.7624	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.7611	Intermediate Similarity	NPD4967	Phase 2
0.7611	Intermediate Similarity	NPD4965	Approved
0.7611	Intermediate Similarity	NPD4966	Approved
0.7588	Intermediate Similarity	NPD2935	Discontinued
0.7556	Intermediate Similarity	NPD3817	Phase 2
0.7553	Intermediate Similarity	NPD7685	Pre-registration
0.7544	Intermediate Similarity	NPD2346	Discontinued
0.7543	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6599	Discontinued
0.7486	Intermediate Similarity	NPD7390	Discontinued
0.7459	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7930	Approved
0.7416	Intermediate Similarity	NPD1653	Approved
0.7399	Intermediate Similarity	NPD1549	Phase 2
0.7399	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6799	Approved
0.7384	Intermediate Similarity	NPD5406	Approved
0.7384	Intermediate Similarity	NPD5405	Approved
0.7384	Intermediate Similarity	NPD5404	Approved
0.7384	Intermediate Similarity	NPD5408	Approved
0.7371	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8059	Phase 3
0.7363	Intermediate Similarity	NPD7680	Approved
0.736	Intermediate Similarity	NPD5403	Approved
0.7358	Intermediate Similarity	NPD8434	Phase 2
0.7356	Intermediate Similarity	NPD6674	Discontinued
0.7337	Intermediate Similarity	NPD8285	Discontinued
0.7323	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD3882	Suspended
0.7314	Intermediate Similarity	NPD7003	Approved
0.7314	Intermediate Similarity	NPD3750	Approved
0.7312	Intermediate Similarity	NPD5711	Approved
0.7312	Intermediate Similarity	NPD5710	Approved
0.7312	Intermediate Similarity	NPD7229	Phase 3
0.7291	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1511	Approved
0.7288	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7584	Approved
0.725	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7177	Discontinued
0.7247	Intermediate Similarity	NPD5401	Approved
0.7247	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7266	Discontinued
0.722	Intermediate Similarity	NPD7585	Approved
0.7207	Intermediate Similarity	NPD1512	Approved
0.7207	Intermediate Similarity	NPD6273	Approved
0.7206	Intermediate Similarity	NPD7999	Approved
0.7184	Intermediate Similarity	NPD1551	Phase 2
0.7184	Intermediate Similarity	NPD2796	Approved
0.7171	Intermediate Similarity	NPD7583	Approved
0.7167	Intermediate Similarity	NPD920	Approved
0.7166	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2799	Discontinued
0.7126	Intermediate Similarity	NPD1510	Phase 2
0.7119	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1607	Approved
0.7076	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7097	Phase 1
0.7068	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD919	Approved
0.7056	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5953	Discontinued
0.7035	Intermediate Similarity	NPD6233	Phase 2
0.7032	Intermediate Similarity	NPD8067	Phase 3
0.7031	Intermediate Similarity	NPD7286	Phase 2
0.7029	Intermediate Similarity	NPD3748	Approved
0.6994	Remote Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD4060	Phase 1
0.6991	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6099	Approved
0.6989	Remote Similarity	NPD6100	Approved
0.6989	Remote Similarity	NPD2438	Suspended
0.6984	Remote Similarity	NPD1247	Approved
0.6983	Remote Similarity	NPD6190	Approved
0.6977	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7985	Registered
0.6977	Remote Similarity	NPD6798	Discontinued
0.6977	Remote Similarity	NPD2313	Discontinued
0.6966	Remote Similarity	NPD1243	Approved
0.6966	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2800	Approved
0.6961	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD447	Suspended
0.6954	Remote Similarity	NPD1933	Approved
0.6949	Remote Similarity	NPD2344	Approved
0.6944	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4287	Approved
0.6932	Remote Similarity	NPD7033	Discontinued
0.6919	Remote Similarity	NPD4625	Phase 3
0.6919	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3926	Phase 2
0.6891	Remote Similarity	NPD7799	Discontinued
0.6882	Remote Similarity	NPD6844	Discontinued
0.6882	Remote Similarity	NPD1203	Approved
0.6879	Remote Similarity	NPD3764	Approved
0.686	Remote Similarity	NPD4908	Phase 1
0.6857	Remote Similarity	NPD6355	Discontinued
0.6857	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5124	Phase 1
0.6845	Remote Similarity	NPD5760	Phase 2
0.6845	Remote Similarity	NPD5761	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