NPASS Compound

Natural Product: NPC709

Natural Product ID	NPC709
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FJMXKFSOKLFYRC-CKNDUULBSA-N
IUPAC Name	n.a.
Synonyms	19-Hydroxywithaferin A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1934449
PubChem CID	56649343
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 73 78 0 0 0 0 0 0 0 0999 V2000 5.8079 -1.9508 0.4515 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8839 -0.9600 -0.2040 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9869 -0.7557 -1.4987 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9985 -1.4826 -2.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3567 -2.2243 -3.3391 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1076 0.2192 -2.1573 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2017 0.4178 -3.4073 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2039 0.8757 -1.3344 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5428 1.0383 0.0063 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8803 -0.2624 0.6381 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6598 1.9477 0.7934 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7345 3.3040 0.1212 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3701 1.4942 1.2622 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6893 2.6399 2.0564 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7899 2.3661 2.0028 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8522 0.9877 1.4692 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1603 0.5609 0.9469 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0475 0.2580 2.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4242 -0.0258 1.6131 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5451 -0.6919 0.4075 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8081 -1.3658 -0.0098 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7660 -2.8145 -0.0987 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6319 -3.4666 -0.1951 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3921 -2.7099 -0.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2678 -3.3231 -0.1296 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3681 -1.2290 -0.3241 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4840 -0.9284 -1.8214 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5520 0.4190 -2.0829 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0476 -0.7529 0.2195 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9536 -0.7195 -0.8233 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3427 -0.3973 -0.0786 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2822 1.0124 0.4179 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1916 1.9714 -0.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2657 -0.7392 -1.1805 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7238 0.7414 0.3936 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8553 -1.6233 0.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4947 -2.1280 1.4881 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6336 -2.9164 -0.0926 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6506 -2.1110 -1.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6346 -0.7437 -2.8464 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9110 -3.0608 -3.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5498 1.6059 -0.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2956 -0.0913 1.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0218 -0.9620 0.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2754 2.1354 1.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7044 4.1557 0.8300 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1142 3.4040 -0.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7984 3.3676 -0.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5398 0.7035 2.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9653 3.6076 1.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0281 2.6106 3.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2242 2.4002 3.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3617 3.1169 1.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5109 0.2836 2.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7329 1.3276 0.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0316 1.1680 2.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6149 -0.6219 2.6732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2421 0.0048 2.3576 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5897 -1.0875 0.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6895 -3.3767 -0.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5580 -4.5488 -0.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5792 -1.3447 -2.3402 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3303 -1.5277 -2.2064 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3498 0.6008 -2.6403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -1.4919 0.9964 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1494 -0.0574 -1.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8273 -1.7918 -1.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1442 -0.6682 -0.7425 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3574 -1.1036 0.7779 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2565 1.8235 -0.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3711 1.8868 -1.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1695 3.0094 -0.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2198 -0.5592 -1.1691 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 4 5 1 0 3 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 11 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 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 6 27 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 21 34 1 0 20 35 1 6 10 2 1 0 32 13 1 0 32 16 1 0 29 17 1 0 35 19 1 0 26 20 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 9 42 1 6 10 43 1 0 10 44 1 0 11 45 1 1 12 46 1 0 12 47 1 0 12 48 1 0 13 49 1 1 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 1 17 55 1 6 18 56 1 0 18 57 1 0 19 58 1 1 21 59 1 1 22 60 1 0 23 61 1 0 27 62 1 0 27 63 1 0 28 64 1 0 29 65 1 1 30 66 1 0 30 67 1 0 31 68 1 0 31 69 1 0 33 70 1 0 33 71 1 0 33 72 1 0 34 73 1 0 M END

Standard InCHIKey	FJMXKFSOKLFYRC-CKNDUULBSA-N
Standard InCHI	InChI=1S/C28H38O7/c1-14-10-21(34-25(33)17(14)12-29)15(2)18-4-5-19-16-11-24-28(35-24)23(32)7-6-22(31)27(28,13-30)20(16)8-9-26(18,19)3/h6-7,15-16,18-21,23-24,29-30,32H,4-5,8-13H2,1-3H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
SMILES	CC1=C(CO)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(CO)[C@H]3CC[C@]12C)O)O4

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.26	Volume:	492.491 ? Van der Waals volume.
Dense:	0.987	LogP:	2.542 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.02 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.972 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	30.0
TPSA:	116.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.412	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.912	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:	0.431	Fluc inhibitor:	0.045 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.172	Promiscuous compounds:	0.782

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.457	MDCK Permeability:	-5.048
Pgp-inhibitor:	0.016	Pgp-substrate:	0.005
PAMPA:	0.109 ? 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):	0.002
20% Bioavailability (F20%):	0.004	30% Bioavailability (F30%):	0.639
50% Bioavailability (F50%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029	MRP1:	0.124
Plasma Protein Binding (PPB):	71.336%	Volume Distribution (VD):	-0.25
Fu:	25.779% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.005
BSEP inhibitor:	0.934

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.638	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.019	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.044	CYP3A4-substrate:	0.17
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.898 ? 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):

8.758

Half-life (T1/2):

1.589

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.12
Human Hepatotoxicity (H-HT):	0.389	Drug-induced Liver Injury (DILI):	0.112
AMES Toxicity:	0.584	Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.614	Skin Sensitization:	0.997
Carcinogencity:	0.95	Eye Corrosion:	0.007
Eye Irritation:	0.781	Respiratory Toxicity:	0.691
Drug-induced Neurotoxicity:	0.056	Ototoxicity:	0.683
Hematotoxicity:	0.405	Drug-induced Nephrotoxicity:	0.729
Genotoxicity:	0.412	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.031	Hek293 Cytotoxicity:	0.358
BCF:	1.059 ? 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:	3.749 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.64 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.802 ? 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
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	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
Activity	15
IC50	9

Activity Type	# Activity
Cell line	7
Single protein	6
Non-molecular	4
Organism	7

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT28585	Single protein	Importin-5	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35772286]
NPT30141	Single protein	Vimentin	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35772286]
NPT29470	Single protein	Annexin A2	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35772286]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[22098611]
NPT170	Cell line	SK-MEL-28	Homo sapiens	IC50	=	5100.0	nM	PMID[22098611]
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	5300.0	nM	PMID[24273633]
NPT170	Cell line	SK-MEL-28	Homo sapiens	IC50	=	1600.0	nM	PMID[24273633]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	1500.0	nM	PMID[24273633]
NPT81	Cell line	A549	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35772286]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	5300.0	nM	PMID[22098611]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3300.0	nM	PMID[22098611]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1700.0	nM	PMID[24273633]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3100.0	nM	PMID[24273633]
NPT742	Organism	Influenza A virus	Influenza A virus	Activity	n.a.	n.a.	n.a.	PMID[35772286]

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 NPC709 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	17269
0.1-0.2	26954
0.2-0.3	5429
0.3-0.4	128
0.4-0.5	35
0.5-0.6	18
0.6-0.7	15
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8906	High Similarity	NPC50774
0.8485	Intermediate Similarity	NPC140055
0.8485	Intermediate Similarity	NPC167606
0.8209	Intermediate Similarity	NPC470265
0.7391	Intermediate Similarity	NPC286528
0.7222	Intermediate Similarity	NPC159456
0.68	Remote Similarity	NPC20302
0.6712	Remote Similarity	NPC284915
0.6712	Remote Similarity	NPC268530
0.6667	Remote Similarity	NPC243065
0.6623	Remote Similarity	NPC470494
0.6622	Remote Similarity	NPC154491
0.6582	Remote Similarity	NPC203702
0.6486	Remote Similarity	NPC122056
0.6364	Remote Similarity	NPC312824
0.6296	Remote Similarity	NPC3381
0.6154	Remote Similarity	NPC264954
0.6133	Remote Similarity	NPC250312
0.6104	Remote Similarity	NPC474370
0.6049	Remote Similarity	NPC120994
0.6047	Remote Similarity	NPC231240
0.5946	Remote Similarity	NPC69291
0.5867	Remote Similarity	NPC67259
0.5867	Remote Similarity	NPC91034
0.5696	Remote Similarity	NPC4021
0.5658	Remote Similarity	NPC474315
0.5641	Remote Similarity	NPC156797
0.56	Remote Similarity	NPC220155
0.5584	Remote Similarity	NPC147912
0.5556	Remote Similarity	NPC470492
0.55	Remote Similarity	NPC183580
0.5417	Remote Similarity	NPC316915
0.5375	Remote Similarity	NPC609580
0.5366	Remote Similarity	NPC251226
0.5309	Remote Similarity	NPC88326
0.5309	Remote Similarity	NPC470493
0.525	Remote Similarity	NPC230513
0.5181	Remote Similarity	NPC67569
0.5128	Remote Similarity	NPC285956

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6238
0.1-0.2	2728
0.2-0.3	182
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate 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