NPASS Compound

Natural Product: NPC286528

Natural Product ID	NPC286528
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HBFRBCZKKTVLPR-NSYRIIBJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2047410
PubChem CID	23266155
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 71 76 0 0 0 0 0 0 0 0999 V2000 5.0913 2.1520 2.1563 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9243 1.0228 1.2082 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9133 0.2847 0.7535 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3028 0.5995 1.2282 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6858 -0.7755 -0.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6675 -1.4441 -0.6114 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3633 -0.9751 -0.6778 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5608 0.1935 -0.6241 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5391 0.6717 0.7945 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3284 0.1583 -1.3903 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7783 -0.0613 -2.8693 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1863 -0.6660 -1.1550 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2662 -2.1580 -1.1513 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1641 -2.5704 -0.7722 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9127 -1.3000 -0.6153 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1190 -1.3100 0.2165 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2502 -1.9926 -0.5154 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3872 -1.1393 -0.9025 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8858 -0.1001 -0.0673 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4147 1.1173 -0.7907 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7913 2.2415 0.0426 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1976 2.4556 1.1941 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1464 1.5465 1.6359 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4352 1.9241 2.5982 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 0.2422 1.0238 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0797 -0.7923 2.1432 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5432 0.1575 0.3862 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4783 1.0143 0.9733 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2949 1.0100 -0.0103 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2105 -0.3934 -0.0570 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5729 -0.8457 1.3035 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4852 0.6996 -1.5852 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5767 -1.2775 -0.0203 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0552 2.0841 2.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2634 2.0962 2.9013 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9707 3.1351 1.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0096 0.0355 0.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4164 0.4684 2.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4477 1.7003 1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2108 0.9917 -1.1470 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2951 -0.1973 1.4882 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8354 1.5139 0.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9635 1.2382 -1.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8640 -0.1235 -3.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2725 -1.0538 -2.9228 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4543 0.7490 -3.1494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5015 -0.4957 -2.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 -2.5904 -0.4103 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4633 -2.5288 -2.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6242 -3.1748 -1.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1751 -3.1032 0.2080 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1613 -0.8514 -1.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0420 -1.7991 1.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8314 -2.4384 -1.4702 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5974 -2.9205 0.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7790 -1.2051 -1.9621 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5771 1.4752 -1.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5716 2.9185 -0.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5174 3.3165 1.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5990 -1.6916 1.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1343 -0.9699 2.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7660 -0.3471 2.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6553 0.5118 -0.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1474 0.6810 1.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8510 2.0600 0.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4784 1.6504 0.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6125 1.3911 -0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2490 -1.2435 1.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3739 -1.6065 1.3451 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9431 0.0497 1.8842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1996 0.5844 -2.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 1 20 32 1 0 19 33 1 1 9 2 1 0 30 12 1 0 30 15 1 0 27 16 1 0 33 18 1 0 25 19 1 0 1 34 1 0 1 35 1 0 1 36 1 0 4 37 1 0 4 38 1 0 4 39 1 0 8 40 1 6 9 41 1 0 9 42 1 0 10 43 1 6 11 44 1 0 11 45 1 0 11 46 1 0 12 47 1 6 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 6 16 53 1 1 17 54 1 0 17 55 1 0 18 56 1 6 20 57 1 6 21 58 1 0 22 59 1 0 26 60 1 0 26 61 1 0 26 62 1 0 27 63 1 6 28 64 1 0 28 65 1 0 29 66 1 0 29 67 1 0 31 68 1 0 31 69 1 0 31 70 1 0 32 71 1 0 M END

Standard InCHIKey	HBFRBCZKKTVLPR-NSYRIIBJSA-N
Standard InCHI	InChI=1S/C28H38O5/c1-14-12-21(32-25(31)15(14)2)16(3)18-6-7-19-17-13-24-28(33-24)23(30)9-8-22(29)27(28,5)20(17)10-11-26(18,19)4/h8-9,16-21,23-24,30H,6-7,10-13H2,1-5H3/t16-,17-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
SMILES	CC1=C(C)C(=O)O[C@H](C1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H]4[C@@]5([C@H](C=CC(=O)[C@]5(C)[C@H]3CC[C@]12C)O)O4

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.27	Volume:	474.911 ? Van der Waals volume.
Dense:	0.957	LogP:	3.435 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.592 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.513 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	30.0
TPSA:	76.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.495	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.635	Fsp³:	0.786
MCE-18:	141.96 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.752	Fluc inhibitor:	0.114 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.195	Promiscuous compounds:	0.393

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.228	MDCK Permeability:	-4.985
Pgp-inhibitor:	0.617	Pgp-substrate:	0.006
PAMPA:	0.019 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.045	30% Bioavailability (F30%):	0.644
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.45
Plasma Protein Binding (PPB):	85.64%	Volume Distribution (VD):	-0.147
Fu:	11.273% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.034
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.996	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.835	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.147	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

12.325

Half-life (T1/2):

1.728

ADMET: Toxicity

hERG Blockers:	0.073	hERG Blockers (10um):	0.334
Human Hepatotoxicity (H-HT):	0.532	Drug-induced Liver Injury (DILI):	0.27
AMES Toxicity:	0.463	Rat Oral Acute Toxicity:	0.296
Maximum Recommended Daily Dose:	0.744	Skin Sensitization:	0.997
Carcinogencity:	0.948	Eye Corrosion:	0.099
Eye Irritation:	0.882	Respiratory Toxicity:	0.756
Drug-induced Neurotoxicity:	0.077	Ototoxicity:	0.47
Hematotoxicity:	0.456	Drug-induced Nephrotoxicity:	0.734
Genotoxicity:	0.673	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.045	Hek293 Cytotoxicity:	0.477
BCF:	1.649 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.268 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.765 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.302 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-013-0297-z]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(75)85035-7]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2015.06.012]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	roots	n.a.	n.a.	PMID[17190461]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19056281]
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22705001]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24079846]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26169123]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30776236]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36350950]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20281	Withania aristata	Species	Solanaceae	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	Organism Name	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
FC	1
IC50	14
Ratio IC50	1
Inhibition	1

Activity Type	# Activity
Individual protein	1
Cell line	11
Non-molecular	4
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4377	Individual protein	Heat shock 70 kDa protein 6	Homo sapiens	FC	=	0.52	n.a.	PMID[11929285]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	4600.0	nM	PMID[20553004]
NPT81	Cell line	A549	Homo sapiens	IC50	=	9000.0	nM	PMID[18980381]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	3400.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	=	1500.0	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	6600.0	nM	PMID[25314007]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1100.0	nM	PMID[25682561]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	1500.0	nM	DrugMatrix in vivo data: Pathology
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	2200.0	nM	PMID[19053514]
NPT189	Cell line	Vero	Chlorocebus aethiops	Ratio IC50	<	1.0	n.a.	PMID[19433554]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	1800.0	nM	PMID[25066952]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	2800.0	nM	PMID[18183025]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	>	80.0	%	PMID[24625088]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	640.0	nM	PMID[24625088]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	880.0	nM	PMID[24625088]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[26169123]
NPT2	Others	Unspecified	n.a.	IC50	=	600.0	nM	PMID[18183025]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC286528 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	17680
0.1-0.2	25984
0.2-0.3	5938
0.3-0.4	149
0.4-0.5	42
0.5-0.6	26
0.6-0.7	25
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC140055
0.875	High Similarity	NPC167606
0.8308	Intermediate Similarity	NPC50774
0.8235	Intermediate Similarity	NPC20302
0.8209	Intermediate Similarity	NPC474370
0.8	Intermediate Similarity	NPC470494
0.7568	Intermediate Similarity	NPC3381
0.7429	Intermediate Similarity	NPC183580
0.7391	Intermediate Similarity	NPC709
0.7286	Intermediate Similarity	NPC609580
0.7183	Intermediate Similarity	NPC88326
0.7	Intermediate Similarity	NPC231240
0.6944	Remote Similarity	NPC470493
0.6622	Remote Similarity	NPC153700
0.6533	Remote Similarity	NPC8369
0.6533	Remote Similarity	NPC312824
0.6533	Remote Similarity	NPC67569
0.6533	Remote Similarity	NPC600975
0.6533	Remote Similarity	NPC602010
0.6438	Remote Similarity	NPC470265
0.6389	Remote Similarity	NPC243065
0.6316	Remote Similarity	NPC264954
0.6316	Remote Similarity	NPC608655
0.6282	Remote Similarity	NPC23786
0.6282	Remote Similarity	NPC473593
0.6234	Remote Similarity	NPC609769
0.6234	Remote Similarity	NPC610140
0.6222	Remote Similarity	NPC316915
0.6216	Remote Similarity	NPC284915
0.6216	Remote Similarity	NPC122056
0.6216	Remote Similarity	NPC268530
0.6154	Remote Similarity	NPC606886
0.6133	Remote Similarity	NPC154491
0.6133	Remote Similarity	NPC473274
0.6	Remote Similarity	NPC270929
0.6	Remote Similarity	NPC30923
0.6	Remote Similarity	NPC610236
0.5921	Remote Similarity	NPC186525
0.5921	Remote Similarity	NPC125794
0.5921	Remote Similarity	NPC171401
0.5897	Remote Similarity	NPC251226
0.5844	Remote Similarity	NPC159456
0.5844	Remote Similarity	NPC470878
0.5769	Remote Similarity	NPC8374
0.5769	Remote Similarity	NPC329671
0.5696	Remote Similarity	NPC470492
0.5641	Remote Similarity	NPC61520
0.5641	Remote Similarity	NPC470495
0.561	Remote Similarity	NPC120994
0.557	Remote Similarity	NPC473253
0.5432	Remote Similarity	NPC604847
0.5375	Remote Similarity	NPC473256
0.5366	Remote Similarity	NPC470880
0.5357	Remote Similarity	NPC203702
0.5316	Remote Similarity	NPC293112
0.5256	Remote Similarity	NPC250312
0.525	Remote Similarity	NPC329736
0.525	Remote Similarity	NPC599946
0.5205	Remote Similarity	NPC273199
0.5122	Remote Similarity	NPC484712
0.5067	Remote Similarity	NPC470496
0.5065	Remote Similarity	NPC69291
0.5062	Remote Similarity	NPC4021

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC286528 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6387
0.1-0.2	2536
0.2-0.3	224
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD7115	Discovery

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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