NPASS Compound

Natural Product: NPC33951

Natural Product ID	NPC33951
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RNNKBVKCPSKXRZ-VZNIDZRDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102206559
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 78 82 0 0 0 0 0 0 0 0999 V2000 -5.5419 4.8359 6.0163 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8296 3.9586 5.0713 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7179 2.7164 5.1948 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2330 4.5375 3.9600 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5352 3.8282 3.0042 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0144 3.5610 1.7463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2606 2.8293 0.8060 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0312 2.3508 1.0898 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5373 2.6248 2.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2785 3.3391 3.2881 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2080 1.5592 0.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5860 0.9776 -0.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7146 0.2451 -1.7935 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0896 -0.2754 -2.8622 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5706 0.1099 -1.3927 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4847 -0.6038 -2.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7905 -0.7400 -1.7114 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1925 -0.1705 -0.5486 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2433 0.5484 0.1867 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9380 0.7102 -0.1942 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0737 1.3839 0.5168 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4771 -0.2962 -0.1082 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4732 -1.0418 -0.7213 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5166 -0.0731 -1.3050 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6210 -0.8903 -1.9143 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2298 -1.8070 -0.8718 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1367 -2.5704 -0.1435 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7720 -3.1641 1.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8058 -4.0337 0.7993 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1379 -1.7359 0.2929 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0471 -2.7215 -1.5154 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6422 -0.0313 -2.3375 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9527 0.7244 -2.2834 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0348 -1.1732 -3.3222 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8929 1.0512 -1.4395 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7753 -0.0391 -1.2745 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7700 0.0354 -0.1724 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8570 -1.0245 -0.3398 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4041 -2.1437 -1.2187 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8518 -1.6163 -2.5022 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9741 -1.6896 -3.5467 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4737 -2.9646 -3.6518 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4223 -0.3156 -2.4841 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4576 -2.9334 -0.5343 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0466 -0.4640 -0.7996 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1514 -0.2416 1.0702 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8147 5.1441 6.8070 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3980 4.3284 6.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9161 5.7580 5.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9810 3.9048 1.4435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6747 2.6724 -0.1815 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5522 2.2562 2.6448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8794 3.5410 4.2845 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4260 -1.3177 -2.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5799 0.9892 1.1046 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1576 -1.6962 -1.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.5200 -0.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2307 -1.4828 -2.7508 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7733 -1.2191 -0.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7752 -3.4028 -0.7703 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2142 -2.2794 1.6585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0152 -3.5871 1.7775 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6812 -4.8851 1.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9810 -2.3970 -1.5470 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0699 0.3875 -1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1023 1.6833 -2.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9007 -0.6553 -4.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1028 -0.9254 -1.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3188 0.9918 -0.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0746 -1.4322 0.6643 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2857 -2.8168 -1.4213 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0703 -2.3316 -2.8400 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7555 -0.9749 -3.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6486 -1.3401 -4.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4600 -2.9052 -3.5553 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7693 -3.1203 0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1355 0.4023 -0.2958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4837 -0.9771 0.9084 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 8 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 18 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 16 34 1 0 12 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 10 5 1 0 21 11 1 0 30 23 1 0 43 36 1 0 20 15 1 0 1 47 1 0 1 48 1 0 1 49 1 0 6 50 1 0 7 51 1 0 9 52 1 0 10 53 1 0 17 54 1 0 19 55 1 0 23 56 1 6 24 57 1 1 25 58 1 6 26 59 1 1 27 60 1 6 28 61 1 0 28 62 1 0 29 63 1 0 31 64 1 0 32 65 1 0 33 66 1 0 34 67 1 0 36 68 1 1 37 69 1 1 38 70 1 1 39 71 1 6 40 72 1 6 41 73 1 0 41 74 1 0 42 75 1 0 44 76 1 0 45 77 1 0 46 78 1 0 M END

Standard InCHIKey	RNNKBVKCPSKXRZ-VZNIDZRDSA-N
Standard InCHI	InChI=1S/C29H32O17/c1-10(32)41-12-4-2-11(3-5-12)26-27(46-29-25(40)23(38)20(35)17(9-31)45-29)21(36)18-14(33)6-13(7-15(18)43-26)42-28-24(39)22(37)19(34)16(8-30)44-28/h2-7,16-17,19-20,22-25,28-31,33-35,37-40H,8-9H2,1H3/t16-,17-,19-,20-,22+,23+,24-,25-,28-,29+/m1/s1
SMILES	CC(=O)Oc1ccc(cc1)c1c(c(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.16	Volume:	593.063 ? Van der Waals volume.
Dense:	1.1	LogP:	0.56 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.268 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.056 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	275.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.717	Fsp³:	0.448
MCE-18:	121.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.62	Fluc inhibitor:	0.324 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.861 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.651 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.163	Promiscuous compounds:	0.4

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.631	MDCK Permeability:	-4.931
Pgp-inhibitor:	0.0	Pgp-substrate:	0.388
PAMPA:	1.0 ? 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):	0.967
20% Bioavailability (F20%):	0.006	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.006
Plasma Protein Binding (PPB):	74.428%	Volume Distribution (VD):	-0.233
Fu:	24.003% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.041
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.525
HLM stability:	0.528 ? 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):

1.523

Half-life (T1/2):

4.82

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.776	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.966	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.064	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.988
Hematotoxicity:	0.307	Drug-induced Nephrotoxicity:	0.766
Genotoxicity:	0.927	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.333	Hek293 Cytotoxicity:	0.16
BCF:	0.364 ? 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:	2.978 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.626 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.607 ? 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
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524113]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8173	Lupinus multiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2383	Mimosa acacioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5425	Polygala nyikensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10340	Crepis rubra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8173	Lupinus multiflorus	Species	Fabaceae	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

Molecular-level activity

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

In vitro activity

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

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 NPC33951 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	17012
0.1-0.2	28705
0.2-0.3	2940
0.3-0.4	674
0.4-0.5	314
0.5-0.6	125
0.6-0.7	60
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC289667
0.8108	Intermediate Similarity	NPC297987
0.7867	Intermediate Similarity	NPC136042
0.7821	Intermediate Similarity	NPC116458
0.7821	Intermediate Similarity	NPC246943
0.775	Intermediate Similarity	NPC251417
0.7595	Intermediate Similarity	NPC605784
0.75	Intermediate Similarity	NPC64425
0.7308	Intermediate Similarity	NPC84362
0.7179	Intermediate Similarity	NPC64305
0.7051	Intermediate Similarity	NPC249281
0.7	Intermediate Similarity	NPC472459
0.6914	Remote Similarity	NPC611303
0.675	Remote Similarity	NPC95090
0.675	Remote Similarity	NPC27408
0.6742	Remote Similarity	NPC35119
0.6737	Remote Similarity	NPC277532
0.6667	Remote Similarity	NPC46420
0.6667	Remote Similarity	NPC470716
0.6667	Remote Similarity	NPC276377
0.6632	Remote Similarity	NPC470715
0.6559	Remote Similarity	NPC14187
0.6556	Remote Similarity	NPC32641
0.6556	Remote Similarity	NPC256188
0.6506	Remote Similarity	NPC285197
0.6479	Remote Similarity	NPC153758
0.6477	Remote Similarity	NPC150164
0.6463	Remote Similarity	NPC271692
0.6458	Remote Similarity	NPC25523
0.6458	Remote Similarity	NPC164704
0.6429	Remote Similarity	NPC22832
0.642	Remote Similarity	NPC77672
0.642	Remote Similarity	NPC133671
0.642	Remote Similarity	NPC135391
0.642	Remote Similarity	NPC78263
0.642	Remote Similarity	NPC250069
0.6364	Remote Similarity	NPC295625
0.6341	Remote Similarity	NPC277205
0.6341	Remote Similarity	NPC158674
0.6341	Remote Similarity	NPC37919
0.6341	Remote Similarity	NPC189142
0.6341	Remote Similarity	NPC77660
0.631	Remote Similarity	NPC60735
0.631	Remote Similarity	NPC26230
0.6289	Remote Similarity	NPC480441
0.6265	Remote Similarity	NPC24043
0.6235	Remote Similarity	NPC243930
0.6235	Remote Similarity	NPC120099
0.6235	Remote Similarity	NPC486578
0.6222	Remote Similarity	NPC186816
0.622	Remote Similarity	NPC261866
0.622	Remote Similarity	NPC39360
0.622	Remote Similarity	NPC29763
0.622	Remote Similarity	NPC210003
0.6196	Remote Similarity	NPC72016
0.6196	Remote Similarity	NPC606657
0.6176	Remote Similarity	NPC470720
0.6145	Remote Similarity	NPC145038
0.6145	Remote Similarity	NPC56077
0.6145	Remote Similarity	NPC281131
0.6145	Remote Similarity	NPC253662
0.6145	Remote Similarity	NPC179950
0.6145	Remote Similarity	NPC323593
0.6145	Remote Similarity	NPC88789
0.6145	Remote Similarity	NPC203500
0.6145	Remote Similarity	NPC491374
0.6118	Remote Similarity	NPC488071
0.6078	Remote Similarity	NPC470717
0.6047	Remote Similarity	NPC21666
0.6024	Remote Similarity	NPC19388
0.6024	Remote Similarity	NPC240431
0.6024	Remote Similarity	NPC55786
0.5978	Remote Similarity	NPC240306
0.5977	Remote Similarity	NPC607707
0.5957	Remote Similarity	NPC5319
0.5952	Remote Similarity	NPC234739
0.5922	Remote Similarity	NPC470719
0.5895	Remote Similarity	NPC76831
0.5882	Remote Similarity	NPC488080
0.5882	Remote Similarity	NPC169977
0.5862	Remote Similarity	NPC148710
0.5862	Remote Similarity	NPC601144
0.5862	Remote Similarity	NPC609478
0.5816	Remote Similarity	NPC121703
0.5814	Remote Similarity	NPC42773
0.5814	Remote Similarity	NPC45522
0.5814	Remote Similarity	NPC325555
0.5814	Remote Similarity	NPC226304
0.5814	Remote Similarity	NPC599850
0.5795	Remote Similarity	NPC311830
0.5765	Remote Similarity	NPC8573
0.5747	Remote Similarity	NPC307938
0.573	Remote Similarity	NPC203050
0.573	Remote Similarity	NPC488072
0.573	Remote Similarity	NPC225434
0.5714	Remote Similarity	NPC480466
0.5698	Remote Similarity	NPC181712
0.5698	Remote Similarity	NPC73511
0.5679	Remote Similarity	NPC134819
0.5663	Remote Similarity	NPC288084
0.5647	Remote Similarity	NPC58053
0.5604	Remote Similarity	NPC480463
0.5581	Remote Similarity	NPC197896
0.5581	Remote Similarity	NPC313163
0.5556	Remote Similarity	NPC191154
0.5556	Remote Similarity	NPC601586
0.5543	Remote Similarity	NPC139320
0.5536	Remote Similarity	NPC223860
0.5529	Remote Similarity	NPC111929
0.5529	Remote Similarity	NPC320283
0.5529	Remote Similarity	NPC41121
0.5517	Remote Similarity	NPC186807
0.5517	Remote Similarity	NPC603655
0.5506	Remote Similarity	NPC101026
0.5506	Remote Similarity	NPC488077
0.5495	Remote Similarity	NPC265115
0.549	Remote Similarity	NPC470712
0.5484	Remote Similarity	NPC275454
0.5465	Remote Similarity	NPC19709
0.5465	Remote Similarity	NPC238376
0.5465	Remote Similarity	NPC143851
0.5464	Remote Similarity	NPC486577
0.5455	Remote Similarity	NPC135358
0.5426	Remote Similarity	NPC156869
0.5412	Remote Similarity	NPC67037
0.5412	Remote Similarity	NPC255615
0.5405	Remote Similarity	NPC262094
0.5393	Remote Similarity	NPC219904
0.5393	Remote Similarity	NPC80140
0.5385	Remote Similarity	NPC190003
0.5385	Remote Similarity	NPC355481
0.5349	Remote Similarity	NPC473043
0.5349	Remote Similarity	NPC331652
0.5341	Remote Similarity	NPC27640
0.5333	Remote Similarity	NPC80188
0.5319	Remote Similarity	NPC471748
0.5306	Remote Similarity	NPC142142
0.5294	Remote Similarity	NPC34531
0.5287	Remote Similarity	NPC127546
0.5287	Remote Similarity	NPC57625
0.5287	Remote Similarity	NPC108831
0.5287	Remote Similarity	NPC173637
0.5287	Remote Similarity	NPC317489
0.5287	Remote Similarity	NPC223424
0.5287	Remote Similarity	NPC182634
0.5287	Remote Similarity	NPC600591
0.5281	Remote Similarity	NPC27942
0.5275	Remote Similarity	NPC220169
0.5269	Remote Similarity	NPC8856
0.5263	Remote Similarity	NPC22062
0.5263	Remote Similarity	NPC473634
0.5263	Remote Similarity	NPC138811
0.5253	Remote Similarity	NPC475382
0.5234	Remote Similarity	NPC470713
0.5227	Remote Similarity	NPC168822
0.5222	Remote Similarity	NPC168584
0.5222	Remote Similarity	NPC175107
0.5217	Remote Similarity	NPC170052
0.5217	Remote Similarity	NPC135846
0.5213	Remote Similarity	NPC29958
0.5172	Remote Similarity	NPC135599
0.5172	Remote Similarity	NPC73855
0.5172	Remote Similarity	NPC113968
0.5172	Remote Similarity	NPC328940
0.5172	Remote Similarity	NPC277174
0.5172	Remote Similarity	NPC160515
0.5172	Remote Similarity	NPC606877
0.5169	Remote Similarity	NPC22195
0.5169	Remote Similarity	NPC21190
0.5165	Remote Similarity	NPC224530
0.5165	Remote Similarity	NPC605067
0.5161	Remote Similarity	NPC116864
0.5161	Remote Similarity	NPC244776
0.5158	Remote Similarity	NPC470405
0.5155	Remote Similarity	NPC46202
0.5155	Remote Similarity	NPC488073
0.5146	Remote Similarity	NPC189564
0.5114	Remote Similarity	NPC44558
0.5111	Remote Similarity	NPC59534
0.5111	Remote Similarity	NPC21100
0.5111	Remote Similarity	NPC60966
0.5109	Remote Similarity	NPC206123
0.5106	Remote Similarity	NPC473682
0.5106	Remote Similarity	NPC278419
0.5106	Remote Similarity	NPC179198
0.5102	Remote Similarity	NPC483414
0.5096	Remote Similarity	NPC48984
0.5091	Remote Similarity	NPC138990
0.5056	Remote Similarity	NPC265530
0.5055	Remote Similarity	NPC159579
0.5055	Remote Similarity	NPC191306
0.5055	Remote Similarity	NPC609451
0.5052	Remote Similarity	NPC115674
0.5052	Remote Similarity	NPC131745
0.5051	Remote Similarity	NPC473623
0.5051	Remote Similarity	NPC209296
0.5045	Remote Similarity	NPC175429

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC33951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4862
0.1-0.2	4191
0.2-0.3	80
0.3-0.4	10
0.4-0.5	3
0.5-0.6	4
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5957	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7808	Phase 3
0.5729	Remote Similarity	NPD7251	Phase 2
0.5051	Remote Similarity	NPD7054	Phase 4

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