NPASS Compound

Structure

CID76682 OpenBabel06191715412D 46 52 0 0 1 0 0 0 0 0999 V2000 2.3291 -4.1877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3783 -0.7232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 -4.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 1.6788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9525 1.6162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7351 1.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1507 -4.5450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0113 -4.0828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5542 -1.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7381 -4.6211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6793 -4.1420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9081 -2.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1759 -1.7433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0221 0.8866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1759 -2.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6014 0.5059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1541 -3.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3661 -1.0457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5874 -2.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 -0.2767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1024 0.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6356 -1.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6454 -3.8026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5894 -1.7020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 -1.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4027 0.5753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3518 -3.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4824 -1.7433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4824 -2.7211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9418 -0.4975 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3113 -3.1905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4824 0.2122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3605 -3.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6356 -0.2767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5965 0.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3626 -0.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3908 0.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6910 0.0553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 -3.2100 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5612 -0.1862 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6714 -4.0996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4824 1.1899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0196 1.7211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5813 0.3613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9332 -3.5961 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 39 1 0 0 0 0 2 40 1 0 0 0 0 3 41 1 0 0 0 0 4 42 1 0 0 0 0 5 43 1 0 0 0 0 6 44 1 0 0 0 0 7 10 1 0 0 0 0 7 23 2 0 0 0 0 8 11 2 0 0 0 0 8 23 1 0 0 0 0 9 12 2 0 0 0 0 9 24 1 0 0 0 0 10 27 2 0 0 0 0 11 27 1 0 0 0 0 12 31 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 39 1 0 0 0 0 16 40 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 24 2 0 0 0 0 19 33 1 0 0 0 0 20 25 2 0 0 0 0 20 32 1 0 0 0 0 21 26 2 0 0 0 0 21 35 1 0 0 0 0 22 28 2 0 0 0 0 22 34 1 0 0 0 0 25 28 1 0 0 0 0 26 36 1 0 0 0 0 27 45 1 0 0 0 0 28 29 1 0 0 0 0 29 17 1 1 0 0 0 29 39 1 0 0 0 0 30 18 1 1 0 0 0 30 36 1 0 0 0 0 30 40 1 0 0 0 0 31 33 2 0 0 0 0 31 41 1 0 0 0 0 32 34 2 0 0 0 0 32 42 1 0 0 0 0 33 45 1 0 0 0 0 34 46 1 0 0 0 0 35 37 2 0 0 0 0 35 43 1 0 0 0 0 36 38 2 0 0 0 0 37 38 1 0 0 0 0 37 44 1 0 0 0 0 38 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.3
Volume:	649.006
LogP:	6.389
LogD:	4.036
LogS:	-6.147
# Rotatable Bonds:	4
TPSA:	61.86
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	5.725
Fsp3:	0.368
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.796
MDCK Permeability:	2.8488837415352464e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.375
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.264
Plasma Protein Binding (PPB):	66.38844299316406%
Volume Distribution (VD):	1.053
Pgp-substrate:	18.580562591552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.978
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.648
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.965
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.96

ADMET: Excretion

Clearance (CL):	9.672
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.975
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.67
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.408
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.482
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.426

Download Data

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

Natural Product: NPC76682

Natural Product ID:	NPC76682
*Common Name:**	WVTKBKWTSCPRNU-XZWHSSHBSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Isotetrandrine; D-Tetrandrine
Standard InCHIKey:	WVTKBKWTSCPRNU-XZWHSSHBSA-N
Standard InCHI:	InChI=1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30+/m0/s1
SMILES:	CN1CCc2cc(c3cc2[C@@H]1Cc1ccc(cc1)Oc1cc(ccc1OC)C[C@@H]1c2c(CCN1C)cc(c(c2O3)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449690
PubChem CID:	457825
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO14431	Dunaliella salina	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14664856]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[25442304]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8450319]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8450319]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	Database[PMID; Title]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14431	Dunaliella salina	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26964	Stephania erecta	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21496	Pilosocereus chrysacanthus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22767	Phomopsis cassiae	Species	Valsaceae	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
ED50	15
IC50	2
Others	24
Potency	26

Activity Type	# Activity
Cell Line	9
Individual Protein	17
Organism	6
Others	34
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	10.0	ug ml-1	PMID[464126]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	11.0	ug ml-1	PMID[464127]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	19.5	ug ml-1	PMID[464127]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	6.6	ug ml-1	PMID[464127]
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.6	ug ml-1	PMID[464127]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	8.4	ug ml-1	PMID[464127]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	9.4	ug ml-1	PMID[464127]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[464127]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	10600.0	nM	PMID[464128]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	35481.3	nM	PMID[464130]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	12589.3	nM	PMID[464129]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	31622.8	nM	PMID[464131]
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	10000.0	nM	PMID[464129]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[464130]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[464130]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[464129]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	3662.6	nM	PMID[464130]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[464129]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[464130]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[464130]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[464130]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[464130]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[464130]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	165.1	ng/ml	PMID[464127]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	54.6	ng/ml	PMID[464127]
NPT27	Others	Unspecified		ED50	=	5.4	ug ml-1	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	33.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	99.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	67.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	202.0	n.a.	PMID[464127]
NPT27	Others	Unspecified		ED50	=	10.0	ug ml-1	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	61.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	183.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	118.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	357.0	n.a.	PMID[464127]
NPT27	Others	Unspecified		ED50	=	10.5	ug ml-1	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	64.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	192.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	40.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	121.0	n.a.	PMID[464127]
NPT27	Others	Unspecified		ED50	=	1.5	ug ml-1	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	9.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	28.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	34.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	103.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	51.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	154.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	57.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	172.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	30.0	n.a.	PMID[464127]
NPT2	Others	Unspecified		Ratio ED50	=	92.0	n.a.	PMID[464127]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	260.0	nM	PMID[464128]
NPT2	Others	Unspecified		Selectivity Index	=	40.0	n.a.	PMID[464128]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	88.0	nM	PMID[464128]
NPT2	Others	Unspecified		Selectivity Index	=	120.0	n.a.	PMID[464128]
NPT2	Others	Unspecified		Potency	=	15848.9	nM	PMID[464129]
NPT2	Others	Unspecified		Potency	=	14581.0	nM	PMID[464130]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[464130]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1471.6	nM	PMID[464130]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[464130]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2332.3	nM	PMID[464130]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[464130]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[464130]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[464130]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[464129]
NPT2	Others	Unspecified		Potency	n.a.	2238.7	nM	PMID[464129]

☑ 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 NPC76682 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	434
0.1-0.2	2015
0.2-0.3	10197
0.3-0.4	8089
0.4-0.5	6310
0.5-0.6	10195
0.6-0.7	4499
0.7-0.8	707
0.8-0.85	118
0.85-0.9	41
0.9-0.95	40
0.95-1	52

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC317145
1.0	High Similarity	NPC227060
1.0	High Similarity	NPC198498
1.0	High Similarity	NPC115284
1.0	High Similarity	NPC10908
1.0	High Similarity	NPC276890
1.0	High Similarity	NPC317439
1.0	High Similarity	NPC63646
0.9937	High Similarity	NPC41376
0.9937	High Similarity	NPC251580
0.9937	High Similarity	NPC129518
0.9937	High Similarity	NPC12424
0.9812	High Similarity	NPC293093
0.9691	High Similarity	NPC243454
0.9691	High Similarity	NPC475479
0.9632	High Similarity	NPC239584
0.9573	High Similarity	NPC182052
0.9573	High Similarity	NPC73492
0.9573	High Similarity	NPC222661
0.9573	High Similarity	NPC258657
0.9573	High Similarity	NPC104196
0.9573	High Similarity	NPC271013
0.9573	High Similarity	NPC15414
0.9573	High Similarity	NPC311973
0.9573	High Similarity	NPC181796
0.9573	High Similarity	NPC328155
0.9573	High Similarity	NPC279228
0.9573	High Similarity	NPC7715
0.9573	High Similarity	NPC185639
0.9573	High Similarity	NPC49075
0.9573	High Similarity	NPC223690
0.9573	High Similarity	NPC42663
0.9573	High Similarity	NPC239824
0.9573	High Similarity	NPC290582
0.9573	High Similarity	NPC217748
0.9573	High Similarity	NPC54654
0.9573	High Similarity	NPC299990
0.9573	High Similarity	NPC229373
0.9573	High Similarity	NPC285931
0.9573	High Similarity	NPC8836
0.9573	High Similarity	NPC290005
0.9573	High Similarity	NPC90998
0.9573	High Similarity	NPC251735
0.9515	High Similarity	NPC274716
0.9515	High Similarity	NPC167116
0.9515	High Similarity	NPC254441
0.9512	High Similarity	NPC286119
0.9458	High Similarity	NPC302245
0.9458	High Similarity	NPC95426
0.9458	High Similarity	NPC16357
0.9455	High Similarity	NPC30779
0.9401	High Similarity	NPC139783
0.9401	High Similarity	NPC116465
0.9401	High Similarity	NPC212237
0.9401	High Similarity	NPC65312
0.9398	High Similarity	NPC302275
0.9345	High Similarity	NPC22115
0.9345	High Similarity	NPC275680
0.9341	High Similarity	NPC249996
0.9299	High Similarity	NPC25084
0.9299	High Similarity	NPC247639
0.929	High Similarity	NPC48490
0.929	High Similarity	NPC206900
0.929	High Similarity	NPC82457
0.929	High Similarity	NPC11296
0.929	High Similarity	NPC175890
0.929	High Similarity	NPC274661
0.929	High Similarity	NPC281581
0.9277	High Similarity	NPC195538
0.9235	High Similarity	NPC475597
0.9235	High Similarity	NPC191132
0.9235	High Similarity	NPC473716
0.9235	High Similarity	NPC60295
0.9222	High Similarity	NPC476202
0.9181	High Similarity	NPC24260
0.9172	High Similarity	NPC14507
0.9172	High Similarity	NPC47077
0.9128	High Similarity	NPC256124
0.907	High Similarity	NPC478093
0.903	High Similarity	NPC10871
0.9017	High Similarity	NPC30182
0.9017	High Similarity	NPC473589
0.9017	High Similarity	NPC478091
0.9017	High Similarity	NPC478092
0.9012	High Similarity	NPC475393
0.8908	High Similarity	NPC85381
0.8902	High Similarity	NPC264850
0.8902	High Similarity	NPC268503
0.8902	High Similarity	NPC42549
0.8902	High Similarity	NPC256012
0.8902	High Similarity	NPC250846
0.8902	High Similarity	NPC318805
0.8902	High Similarity	NPC41122
0.8902	High Similarity	NPC240841
0.8902	High Similarity	NPC317272
0.8902	High Similarity	NPC13916
0.887	High Similarity	NPC475654
0.8841	High Similarity	NPC24465
0.8807	High Similarity	NPC234318
0.8795	High Similarity	NPC83198
0.8795	High Similarity	NPC204908
0.879	High Similarity	NPC210437
0.879	High Similarity	NPC476144
0.879	High Similarity	NPC106295
0.879	High Similarity	NPC51957
0.879	High Similarity	NPC16107
0.8734	High Similarity	NPC7467
0.8722	High Similarity	NPC254581
0.8642	High Similarity	NPC123323
0.8639	High Similarity	NPC190783
0.8639	High Similarity	NPC232386
0.8639	High Similarity	NPC152680
0.858	High Similarity	NPC475215
0.858	High Similarity	NPC108434
0.8535	High Similarity	NPC136860
0.8535	High Similarity	NPC128019
0.8535	High Similarity	NPC476567
0.8424	Intermediate Similarity	NPC476572
0.8415	Intermediate Similarity	NPC249797
0.8415	Intermediate Similarity	NPC295691
0.8415	Intermediate Similarity	NPC127674
0.8415	Intermediate Similarity	NPC469817
0.8415	Intermediate Similarity	NPC325871
0.8415	Intermediate Similarity	NPC276588
0.8415	Intermediate Similarity	NPC99659
0.8415	Intermediate Similarity	NPC2413
0.8415	Intermediate Similarity	NPC138487
0.8415	Intermediate Similarity	NPC278799
0.8415	Intermediate Similarity	NPC5238
0.8415	Intermediate Similarity	NPC184026
0.8415	Intermediate Similarity	NPC204828
0.8415	Intermediate Similarity	NPC216459
0.8415	Intermediate Similarity	NPC54379
0.8415	Intermediate Similarity	NPC207757
0.8415	Intermediate Similarity	NPC193949
0.8415	Intermediate Similarity	NPC110416
0.8415	Intermediate Similarity	NPC39701
0.8415	Intermediate Similarity	NPC172765
0.8415	Intermediate Similarity	NPC189266
0.8415	Intermediate Similarity	NPC41178
0.8408	Intermediate Similarity	NPC213206
0.8408	Intermediate Similarity	NPC188163
0.8408	Intermediate Similarity	NPC328750
0.8408	Intermediate Similarity	NPC474915
0.8402	Intermediate Similarity	NPC204947
0.8364	Intermediate Similarity	NPC146288
0.8363	Intermediate Similarity	NPC19520
0.8363	Intermediate Similarity	NPC149090
0.8363	Intermediate Similarity	NPC239775
0.8344	Intermediate Similarity	NPC314682
0.8333	Intermediate Similarity	NPC92541
0.8323	Intermediate Similarity	NPC230956
0.8323	Intermediate Similarity	NPC271388
0.8323	Intermediate Similarity	NPC235143
0.8323	Intermediate Similarity	NPC119649
0.8323	Intermediate Similarity	NPC205255
0.8304	Intermediate Similarity	NPC118274
0.8304	Intermediate Similarity	NPC168753
0.8303	Intermediate Similarity	NPC244112
0.8303	Intermediate Similarity	NPC187022
0.8303	Intermediate Similarity	NPC80129
0.8286	Intermediate Similarity	NPC257269
0.8286	Intermediate Similarity	NPC230276
0.8274	Intermediate Similarity	NPC80759
0.8274	Intermediate Similarity	NPC79402
0.8263	Intermediate Similarity	NPC221864
0.8263	Intermediate Similarity	NPC7393
0.8253	Intermediate Similarity	NPC234392
0.8253	Intermediate Similarity	NPC31311
0.8232	Intermediate Similarity	NPC326316
0.8232	Intermediate Similarity	NPC81733
0.8229	Intermediate Similarity	NPC119068
0.8229	Intermediate Similarity	NPC40496
0.822	Intermediate Similarity	NPC38964
0.821	Intermediate Similarity	NPC476151
0.821	Intermediate Similarity	NPC144863
0.8198	Intermediate Similarity	NPC75958
0.8171	Intermediate Similarity	NPC97221
0.8171	Intermediate Similarity	NPC151895
0.8171	Intermediate Similarity	NPC192768
0.8171	Intermediate Similarity	NPC220858
0.8171	Intermediate Similarity	NPC88249
0.8166	Intermediate Similarity	NPC60186
0.8156	Intermediate Similarity	NPC208890
0.8155	Intermediate Similarity	NPC216816
0.8148	Intermediate Similarity	NPC473934
0.8144	Intermediate Similarity	NPC180756
0.8144	Intermediate Similarity	NPC323443
0.8135	Intermediate Similarity	NPC82056
0.8129	Intermediate Similarity	NPC24264
0.8129	Intermediate Similarity	NPC476432
0.8125	Intermediate Similarity	NPC474507
0.8114	Intermediate Similarity	NPC241704
0.811	Intermediate Similarity	NPC103379
0.811	Intermediate Similarity	NPC477565
0.8103	Intermediate Similarity	NPC2314
0.8086	Intermediate Similarity	NPC185838
0.8081	Intermediate Similarity	NPC145832
0.8081	Intermediate Similarity	NPC158376
0.8081	Intermediate Similarity	NPC117188

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 NPC76682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	848
0.2-0.3	1112
0.3-0.4	2288
0.4-0.5	2384
0.5-0.6	1564
0.6-0.7	595
0.7-0.8	115
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8252	Approved
1.0	High Similarity	NPD8251	Approved
1.0	High Similarity	NPD8099	Discontinued
0.9937	High Similarity	NPD8156	Discontinued
0.9573	High Similarity	NPD8054	Approved
0.9573	High Similarity	NPD8053	Approved
0.892	High Similarity	NPD8095	Phase 1
0.879	High Similarity	NPD4584	Approved
0.8712	High Similarity	NPD6788	Approved
0.8408	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7298	Approved
0.8232	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4773	Phase 2
0.8133	Intermediate Similarity	NPD4772	Phase 2
0.8033	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1424	Approved
0.7987	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6071	Discontinued
0.7914	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6030	Approved
0.7892	Intermediate Similarity	NPD6031	Approved
0.7866	Intermediate Similarity	NPD7124	Phase 2
0.7816	Intermediate Similarity	NPD3051	Approved
0.7803	Intermediate Similarity	NPD5677	Discontinued
0.7803	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7906	Approved
0.7798	Intermediate Similarity	NPD4017	Approved
0.7791	Intermediate Similarity	NPD7833	Phase 2
0.7791	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7831	Phase 2
0.7784	Intermediate Similarity	NPD3640	Phase 3
0.7784	Intermediate Similarity	NPD3639	Approved
0.7784	Intermediate Similarity	NPD3641	Approved
0.7759	Intermediate Similarity	NPD7802	Discontinued
0.7759	Intermediate Similarity	NPD6107	Approved
0.7727	Intermediate Similarity	NPD4481	Phase 3
0.7688	Intermediate Similarity	NPD4055	Discovery
0.7674	Intermediate Similarity	NPD2563	Approved
0.7674	Intermediate Similarity	NPD2560	Approved
0.7673	Intermediate Similarity	NPD4475	Approved
0.7673	Intermediate Similarity	NPD4474	Approved
0.767	Intermediate Similarity	NPD2969	Approved
0.767	Intermediate Similarity	NPD2970	Approved
0.7665	Intermediate Similarity	NPD7447	Phase 1
0.7636	Intermediate Similarity	NPD6748	Discontinued
0.7624	Intermediate Similarity	NPD7549	Discontinued
0.761	Intermediate Similarity	NPD5718	Phase 2
0.7605	Intermediate Similarity	NPD7598	Phase 2
0.7595	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2200	Suspended
0.7582	Intermediate Similarity	NPD7313	Approved
0.7582	Intermediate Similarity	NPD7312	Approved
0.7582	Intermediate Similarity	NPD7311	Approved
0.7582	Intermediate Similarity	NPD7310	Approved
0.7541	Intermediate Similarity	NPD7309	Approved
0.753	Intermediate Similarity	NPD7466	Approved
0.7528	Intermediate Similarity	NPD27	Approved
0.7528	Intermediate Similarity	NPD2489	Approved
0.7515	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5005	Approved
0.75	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD3124	Discontinued
0.75	Intermediate Similarity	NPD5313	Approved
0.75	Intermediate Similarity	NPD7213	Phase 3
0.75	Intermediate Similarity	NPD5006	Approved
0.75	Intermediate Similarity	NPD5312	Approved
0.7486	Intermediate Similarity	NPD4577	Approved
0.7486	Intermediate Similarity	NPD4578	Approved
0.7485	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4663	Approved
0.7456	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4675	Approved
0.7442	Intermediate Similarity	NPD4678	Approved
0.7391	Intermediate Similarity	NPD2968	Approved
0.7391	Intermediate Similarity	NPD2971	Approved
0.7384	Intermediate Similarity	NPD4005	Discontinued
0.7381	Intermediate Similarity	NPD5241	Discontinued
0.7378	Intermediate Similarity	NPD6895	Approved
0.7378	Intermediate Similarity	NPD6111	Discontinued
0.7378	Intermediate Similarity	NPD6896	Approved
0.7337	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4010	Discontinued
0.7318	Intermediate Similarity	NPD4166	Phase 2
0.7314	Intermediate Similarity	NPD4585	Approved
0.7292	Intermediate Similarity	NPD4420	Approved
0.7288	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD2973	Approved
0.724	Intermediate Similarity	NPD2975	Approved
0.724	Intermediate Similarity	NPD2974	Approved
0.7238	Intermediate Similarity	NPD2898	Approved
0.7234	Intermediate Similarity	NPD7291	Discontinued
0.7219	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5773	Approved
0.7216	Intermediate Similarity	NPD5772	Approved
0.7209	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2420	Approved
0.7193	Intermediate Similarity	NPD2421	Approved
0.7178	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2122	Discontinued
0.7168	Intermediate Similarity	NPD5976	Discontinued
0.7166	Intermediate Similarity	NPD6851	Approved
0.7166	Intermediate Similarity	NPD6853	Approved
0.716	Intermediate Similarity	NPD5177	Phase 3
0.7159	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4123	Phase 3
0.7151	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6297	Approved
0.7128	Intermediate Similarity	NPD4580	Approved
0.7125	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5089	Approved
0.7102	Intermediate Similarity	NPD7110	Phase 1
0.7102	Intermediate Similarity	NPD5090	Approved
0.7102	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6072	Discontinued
0.7092	Intermediate Similarity	NPD2494	Approved
0.7092	Intermediate Similarity	NPD3452	Approved
0.7092	Intermediate Similarity	NPD3450	Approved
0.7092	Intermediate Similarity	NPD2493	Approved
0.7091	Intermediate Similarity	NPD3109	Approved
0.7091	Intermediate Similarity	NPD3110	Approved
0.7088	Intermediate Similarity	NPD5242	Approved
0.7074	Intermediate Similarity	NPD6618	Phase 2
0.7068	Intermediate Similarity	NPD2490	Approved
0.7068	Intermediate Similarity	NPD2488	Approved
0.7062	Intermediate Similarity	NPD3384	Approved
0.7062	Intermediate Similarity	NPD5720	Discontinued
0.7062	Intermediate Similarity	NPD3383	Approved
0.7062	Intermediate Similarity	NPD3382	Approved
0.7059	Intermediate Similarity	NPD4236	Phase 3
0.7059	Intermediate Similarity	NPD4237	Approved
0.7059	Intermediate Similarity	NPD4162	Approved
0.7041	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3845	Phase 1
0.7029	Intermediate Similarity	NPD4210	Discontinued
0.7022	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6997	Phase 2
0.7018	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5938	Phase 3
0.7011	Intermediate Similarity	NPD6090	Discontinued
0.6995	Remote Similarity	NPD6687	Approved
0.6995	Remote Similarity	NPD6688	Approved
0.6994	Remote Similarity	NPD5297	Approved
0.6994	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4582	Approved
0.6985	Remote Similarity	NPD4583	Approved
0.6984	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5978	Approved
0.6983	Remote Similarity	NPD5977	Approved
0.6977	Remote Similarity	NPD5160	Discontinued
0.6977	Remote Similarity	NPD3692	Discontinued
0.6976	Remote Similarity	NPD7047	Phase 3
0.6975	Remote Similarity	NPD4098	Discontinued
0.6973	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4908	Phase 1
0.6937	Remote Similarity	NPD8153	Approved
0.6937	Remote Similarity	NPD8152	Approved
0.6936	Remote Similarity	NPD6666	Approved
0.6936	Remote Similarity	NPD6667	Approved
0.6935	Remote Similarity	NPD42	Phase 2
0.6935	Remote Similarity	NPD6042	Phase 2
0.6935	Remote Similarity	NPD4004	Approved
0.6935	Remote Similarity	NPD4002	Approved
0.6933	Remote Similarity	NPD7905	Discontinued
0.6927	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5754	Discontinued
0.6919	Remote Similarity	NPD3489	Phase 3
0.691	Remote Similarity	NPD6386	Approved
0.691	Remote Similarity	NPD6385	Approved
0.6907	Remote Similarity	NPD7125	Discontinued
0.6906	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6357	Discontinued
0.6891	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7034	Discontinued
0.6886	Remote Similarity	NPD2238	Phase 2
0.6884	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2677	Approved
0.6867	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.686	Remote Similarity	NPD44	Approved
0.686	Remote Similarity	NPD3060	Approved
0.686	Remote Similarity	NPD6364	Approved
0.6859	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6876	Approved
0.6854	Remote Similarity	NPD6875	Approved
0.6848	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3656	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