NPASS Compound

Natural Product: NPC256215

Natural Product ID	NPC256215
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ULOAWPSYNSJWGI-FLSZNSENSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	51136540
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 89 94 0 0 0 0 0 0 0 0999 V2000 9.4579 -0.3613 -0.8790 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6062 0.1012 0.3136 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4468 1.5966 0.1519 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4086 2.1456 1.1094 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9458 0.9690 1.9574 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3793 -0.0537 0.9910 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4308 -0.5886 0.2512 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5960 -1.0151 1.6034 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2691 -1.3222 1.4001 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6683 -2.3609 2.1399 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3418 -2.6727 1.9398 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5806 -1.9781 1.0170 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1441 -0.9557 0.2790 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4793 -0.6605 0.4975 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4200 -0.3100 -0.5854 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1185 -0.5776 -0.8172 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5528 0.2473 -1.8381 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0499 1.4446 -2.2110 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4153 2.2785 -3.1975 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5698 1.8648 -3.8449 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1852 0.6892 -3.4985 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6880 -0.1228 -2.5030 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0832 2.6692 -4.8481 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4927 -1.5539 -0.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2569 -2.2856 0.8175 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3252 -3.1978 1.4485 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8358 -1.8959 -0.2803 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8146 -1.3943 0.6076 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0218 -0.8599 -0.0134 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2841 -1.5935 0.4817 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0532 -3.0669 0.3319 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7721 -3.4876 1.0088 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0188 -4.4512 0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9573 -5.4290 -0.2653 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0529 -2.4446 1.5158 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1554 -3.7317 0.8295 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3559 -1.2582 -0.3494 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1587 0.4959 0.3308 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3646 1.3301 -0.7344 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6804 2.0630 -0.5578 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2492 3.2581 0.2707 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5912 2.9227 1.7243 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9782 2.7160 1.8377 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7649 3.3161 0.1057 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3974 2.3381 -0.8205 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9144 4.4090 -0.1222 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2084 2.4640 -1.7814 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7608 -3.6982 2.6748 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0158 1.3723 2.9079 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3102 2.5554 0.3355 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6735 2.1828 0.4805 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9205 -0.1823 -1.8373 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4449 0.1001 -0.8813 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6140 -1.4732 -0.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2357 -0.1422 1.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2428 1.8693 -0.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8023 2.9674 1.7261 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8274 0.5756 2.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7786 0.5239 0.2668 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2959 -2.8873 2.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8790 0.1388 -0.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9508 1.7330 -1.6786 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0959 3.1912 -3.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0992 0.4038 -4.0441 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1741 -1.0456 -2.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6727 2.6851 -5.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2949 -0.6189 1.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0946 -0.9068 -1.1071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4572 -1.2547 1.5108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -3.2842 -0.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1048 -4.0974 1.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6029 -4.0209 -0.7820 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2528 -4.9970 0.7361 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2550 -5.2081 -1.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5227 -4.3893 0.1883 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2122 -1.4904 0.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4101 0.8077 -1.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4366 1.4565 -0.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3120 3.7180 2.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0866 1.9935 1.9983 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1721 2.3406 2.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2064 3.2499 1.0553 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5298 4.3279 -0.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3883 5.2241 0.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4713 3.3977 -1.8100 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5838 -4.6239 2.2718 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5577 2.2130 2.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4739 2.4373 -0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6234 3.1656 0.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 16 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 44 45 1 0 41 46 1 6 40 47 1 0 11 48 1 0 5 49 1 0 4 50 1 0 3 51 1 0 7 2 1 0 14 9 1 0 22 17 1 0 35 28 1 0 45 39 1 0 25 12 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 1 3 56 1 6 4 57 1 1 5 58 1 1 6 59 1 6 10 60 1 0 14 61 1 0 18 62 1 0 19 63 1 0 21 64 1 0 22 65 1 0 23 66 1 0 28 67 1 1 29 68 1 6 30 69 1 1 31 70 1 6 32 71 1 1 33 72 1 0 33 73 1 0 34 74 1 0 36 75 1 0 37 76 1 0 39 77 1 6 40 78 1 1 42 79 1 0 42 80 1 0 43 81 1 0 44 82 1 0 44 83 1 0 46 84 1 0 47 85 1 0 48 86 1 0 49 87 1 0 50 88 1 0 51 89 1 0 M END

Standard InCHIKey	ULOAWPSYNSJWGI-FLSZNSENSA-N
Standard InCHI	InChI=1S/C32H38O19/c1-11-19(37)22(40)24(42)29(46-11)47-14-6-15(36)18-16(7-14)48-25(12-2-4-13(35)5-3-12)26(21(18)39)50-30-27(23(41)20(38)17(8-33)49-30)51-31-28(43)32(44,9-34)10-45-31/h2-7,11,17,19-20,22-24,27-31,33-38,40-44H,8-10H2,1H3/t11-,17+,19-,20+,22+,23-,24+,27+,28-,29-,30-,31-,32+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)oc(c1ccc(cc1)O)c(c2=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	726.2	Volume:	656.612 ? Van der Waals volume.
Dense:	1.106	LogP:	1.021 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.341 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.555 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	35.0
TPSA:	308.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.103	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.31	Fsp³:	0.531
MCE-18:	150.0 ? 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:	0.608	Fluc inhibitor:	0.267 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.689 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.562 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.174	Promiscuous compounds:	0.571

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.749	MDCK Permeability:	-4.979
Pgp-inhibitor:	0.0	Pgp-substrate:	0.853
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):	0.99
20% Bioavailability (F20%):	0.606	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.078
Plasma Protein Binding (PPB):	82.481%	Volume Distribution (VD):	-0.013
Fu:	17.582% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.282
BSEP inhibitor:	0.0

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:	0.008
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.757
HLM stability:	0.031 ? 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):

1.198

Half-life (T1/2):

5.025

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.029
Human Hepatotoxicity (H-HT):	0.777	Drug-induced Liver Injury (DILI):	0.984
AMES Toxicity:	0.967	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.011	Skin Sensitization:	1.0
Carcinogencity:	0.073	Eye Corrosion:	0.0
Eye Irritation:	0.067	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.989
Hematotoxicity:	0.141	Drug-induced Nephrotoxicity:	0.803
Genotoxicity:	0.951	RPMI-8226 Immunitoxicity:	0.262
A549 Cytotoxicity:	0.915	Hek293 Cytotoxicity:	0.774
BCF:	0.371 ? 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:	2.876 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.586 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.571 ? 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
NPO29504	Urena lobata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29504	Urena lobata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29504	Urena lobata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29504	Urena lobata	Species	Malvaceae	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 NPC256215 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	22515
0.1-0.2	23896
0.2-0.3	2659
0.3-0.4	354
0.4-0.5	275
0.5-0.6	102
0.6-0.7	32
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC32641
0.8462	Intermediate Similarity	NPC256188
0.8462	Intermediate Similarity	NPC35119
0.7826	Intermediate Similarity	NPC150164
0.766	Intermediate Similarity	NPC240306
0.7525	Intermediate Similarity	NPC25523
0.7474	Intermediate Similarity	NPC64425
0.7363	Intermediate Similarity	NPC116458
0.7363	Intermediate Similarity	NPC246943
0.7097	Intermediate Similarity	NPC276377
0.7079	Intermediate Similarity	NPC249281
0.701	Intermediate Similarity	NPC122809
0.6857	Remote Similarity	NPC480441
0.6813	Remote Similarity	NPC297987
0.68	Remote Similarity	NPC72016
0.6796	Remote Similarity	NPC14187
0.6739	Remote Similarity	NPC46420
0.6733	Remote Similarity	NPC142142
0.6667	Remote Similarity	NPC186816
0.6633	Remote Similarity	NPC163242
0.6633	Remote Similarity	NPC272068
0.6632	Remote Similarity	NPC605784
0.6542	Remote Similarity	NPC164704
0.64	Remote Similarity	NPC65003
0.6263	Remote Similarity	NPC251417
0.6239	Remote Similarity	NPC470715
0.6239	Remote Similarity	NPC303694
0.6238	Remote Similarity	NPC304741
0.6224	Remote Similarity	NPC170052
0.6224	Remote Similarity	NPC135846
0.6214	Remote Similarity	NPC480471
0.6214	Remote Similarity	NPC488076
0.6195	Remote Similarity	NPC470717
0.6176	Remote Similarity	NPC470444
0.617	Remote Similarity	NPC289667
0.6105	Remote Similarity	NPC136042
0.61	Remote Similarity	NPC473682
0.6087	Remote Similarity	NPC209550
0.6078	Remote Similarity	NPC155877
0.6075	Remote Similarity	NPC602448
0.6042	Remote Similarity	NPC271692
0.6038	Remote Similarity	NPC76831
0.6019	Remote Similarity	NPC115674
0.6	Remote Similarity	NPC470720
0.5918	Remote Similarity	NPC611303
0.59	Remote Similarity	NPC476215
0.5876	Remote Similarity	NPC84362
0.5763	Remote Similarity	NPC175429
0.5755	Remote Similarity	NPC12013
0.5755	Remote Similarity	NPC11432
0.5755	Remote Similarity	NPC477613
0.5741	Remote Similarity	NPC473071
0.5741	Remote Similarity	NPC220173
0.5739	Remote Similarity	NPC295625
0.5729	Remote Similarity	NPC111929
0.5729	Remote Similarity	NPC320283
0.5729	Remote Similarity	NPC331652
0.5729	Remote Similarity	NPC41121
0.5714	Remote Similarity	NPC219043
0.5714	Remote Similarity	NPC255157
0.5714	Remote Similarity	NPC259896
0.57	Remote Similarity	NPC224530
0.5688	Remote Similarity	NPC292929
0.5688	Remote Similarity	NPC221342
0.5688	Remote Similarity	NPC476470
0.5686	Remote Similarity	NPC254855
0.5686	Remote Similarity	NPC94610
0.5678	Remote Similarity	NPC138990
0.5673	Remote Similarity	NPC470405
0.567	Remote Similarity	NPC108831
0.567	Remote Similarity	NPC182634
0.5631	Remote Similarity	NPC8856
0.5625	Remote Similarity	NPC488075
0.5612	Remote Similarity	NPC158674
0.5607	Remote Similarity	NPC65711
0.5596	Remote Similarity	NPC195257
0.5536	Remote Similarity	NPC121703
0.551	Remote Similarity	NPC39360
0.551	Remote Similarity	NPC77672
0.551	Remote Similarity	NPC133671
0.551	Remote Similarity	NPC135391
0.551	Remote Similarity	NPC29763
0.551	Remote Similarity	NPC78263
0.551	Remote Similarity	NPC210003
0.551	Remote Similarity	NPC250069
0.5508	Remote Similarity	NPC470719
0.55	Remote Similarity	NPC192539
0.5455	Remote Similarity	NPC323593
0.5455	Remote Similarity	NPC203500
0.5439	Remote Similarity	NPC48984
0.5424	Remote Similarity	NPC298666
0.5413	Remote Similarity	NPC606657
0.54	Remote Similarity	NPC24043
0.5385	Remote Similarity	NPC95866
0.5377	Remote Similarity	NPC173582
0.5377	Remote Similarity	NPC44931
0.5377	Remote Similarity	NPC265885
0.5377	Remote Similarity	NPC181465
0.5377	Remote Similarity	NPC215710
0.5377	Remote Similarity	NPC473438
0.5377	Remote Similarity	NPC253788
0.5354	Remote Similarity	NPC19709
0.5354	Remote Similarity	NPC238376
0.5351	Remote Similarity	NPC473072
0.5345	Remote Similarity	NPC277532
0.5317	Remote Similarity	NPC223860
0.5299	Remote Similarity	NPC470716
0.5294	Remote Similarity	NPC480445
0.5273	Remote Similarity	NPC122467
0.5259	Remote Similarity	NPC470712
0.52	Remote Similarity	NPC127546
0.52	Remote Similarity	NPC57625
0.52	Remote Similarity	NPC173637
0.52	Remote Similarity	NPC317489
0.52	Remote Similarity	NPC223424
0.52	Remote Similarity	NPC348541
0.52	Remote Similarity	NPC600591
0.5196	Remote Similarity	NPC216496
0.5182	Remote Similarity	NPC483414
0.5169	Remote Similarity	NPC255799
0.5161	Remote Similarity	NPC199172
0.5149	Remote Similarity	NPC64305
0.5149	Remote Similarity	NPC277205
0.5149	Remote Similarity	NPC37919
0.5149	Remote Similarity	NPC189142
0.5149	Remote Similarity	NPC77660
0.514	Remote Similarity	NPC480466
0.514	Remote Similarity	NPC139320
0.513	Remote Similarity	NPC203145
0.5098	Remote Similarity	NPC27640
0.5098	Remote Similarity	NPC488080
0.5098	Remote Similarity	NPC169977
0.5093	Remote Similarity	NPC67105
0.5088	Remote Similarity	NPC253685
0.5086	Remote Similarity	NPC189564
0.5085	Remote Similarity	NPC311850
0.5083	Remote Similarity	NPC488739
0.5051	Remote Similarity	NPC288084
0.5049	Remote Similarity	NPC472459
0.5049	Remote Similarity	NPC59534
0.5046	Remote Similarity	NPC65563
0.5046	Remote Similarity	NPC210073
0.5046	Remote Similarity	NPC470949
0.5044	Remote Similarity	NPC475382
0.5041	Remote Similarity	NPC198199
0.504	Remote Similarity	NPC25946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC256215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5943
0.1-0.2	3166
0.2-0.3	33
0.3-0.4	2
0.4-0.5	4
0.5-0.6	2
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
0.5596	Remote Similarity	NPD7251	Phase 2
0.5263	Remote Similarity	NPD7808	Phase 3

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