NPASS Compound

Natural Product: NPC87655

Natural Product ID	NPC87655
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IETHJOSAGYFEFJ-YNPHYVAESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 8.5201 -3.0312 -3.1237 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8505 -3.3449 -1.8022 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7255 -2.9264 -0.6417 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1438 -3.6354 0.5827 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6628 -3.3855 0.5853 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2592 -2.3444 -0.4419 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6628 -2.6730 -1.7344 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8602 -2.2995 -0.4396 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0502 -1.2557 -0.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5282 -0.0558 0.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6459 0.9417 0.7908 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2650 0.8069 0.7153 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8044 -0.4151 0.2362 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6669 -1.4189 -0.1364 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5192 -0.5630 0.1574 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3554 0.3891 0.5088 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7407 0.0084 0.3403 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0958 -1.0716 -0.4542 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 -1.4746 -0.5728 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4451 -0.8674 0.0647 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0912 0.2207 0.8672 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7647 0.6327 0.9894 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7687 -1.1908 0.0112 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2831 -2.2360 -0.7439 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0495 -3.1903 0.1629 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2760 -3.5381 -0.6128 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5276 -3.2182 0.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4843 -1.8841 0.5732 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1628 -2.6907 -1.8513 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2571 -1.6849 -1.5898 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2956 -4.8751 -1.0187 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2480 -4.3308 0.3465 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0398 1.5887 0.9738 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4239 1.8105 1.0850 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8487 2.8957 1.5098 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8129 2.6400 1.3460 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1466 3.6452 0.3723 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5574 4.0493 0.5283 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7559 5.5535 0.3892 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7596 6.0603 -0.6037 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3468 5.7217 -0.2453 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3577 6.9245 0.3428 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6983 6.5395 0.5725 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2565 4.6968 0.6890 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1378 5.6146 -1.8677 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6012 6.1400 1.6522 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3467 3.4569 -0.4687 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0993 2.1779 1.2757 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3600 -2.8010 1.8360 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7791 -3.2889 1.7504 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0555 -3.2869 -0.8490 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1898 -3.8669 -3.4130 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7469 -2.9520 -3.8956 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0962 -2.0778 -3.0127 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6314 -4.4494 -1.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6170 -1.8401 -0.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2991 -4.7266 0.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0700 -4.3036 0.5030 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6609 -1.3922 -0.0991 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5888 0.1453 0.5159 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2651 -2.3518 -0.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3088 -1.5848 -0.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6396 -2.3349 -1.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8488 0.7541 1.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5795 1.4713 1.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5159 -2.7705 -1.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2186 -2.7370 1.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5216 -3.8797 1.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3983 -3.4596 -0.4391 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1276 -1.2914 -0.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8567 -3.3123 -2.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1573 -2.2158 -2.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4296 -5.3097 -0.8144 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2855 -4.0494 0.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8819 3.2158 -0.6129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0338 3.7694 1.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7790 5.7221 0.0401 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8448 7.1814 -0.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1974 5.4619 -1.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3347 7.8037 -0.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0700 7.1080 1.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9589 5.8877 -0.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7480 6.2727 -2.3090 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8498 5.6697 2.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3129 3.6531 -0.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0081 2.4968 0.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1721 -3.4745 2.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2114 -3.3132 2.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4958 -2.4563 -1.2140 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 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 29 30 1 0 26 31 1 6 25 32 1 0 16 33 2 0 33 34 1 0 34 35 2 0 33 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 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 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 30 24 1 0 44 37 1 0 34 12 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 1 3 56 1 1 4 57 1 6 5 58 1 6 6 59 1 1 10 60 1 0 14 61 1 0 18 62 1 0 19 63 1 0 21 64 1 0 22 65 1 0 24 66 1 6 25 67 1 1 27 68 1 0 27 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 31 73 1 0 32 74 1 0 37 75 1 6 38 76 1 1 39 77 1 6 40 78 1 6 41 79 1 6 42 80 1 0 42 81 1 0 43 82 1 0 45 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	IETHJOSAGYFEFJ-YNPHYVAESA-N
Standard InCHI	InChI=1S/C32H38O19/c1-11-19(36)22(39)24(41)29(46-11)48-14-6-15(35)18-16(7-14)49-26(27(21(18)38)51-30-25(42)23(40)20(37)17(8-33)50-30)12-2-4-13(5-3-12)47-31-28(43)32(44,9-34)10-45-31/h2-7,11,17,19-20,22-25,28-31,33-37,39-44H,8-10H2,1H3/t11-,17+,19-,20+,22+,23-,24+,25+,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@H]1[C@@H]([C@@](CO)(CO1)O)O)c(c2=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)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:	1.197 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.66 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.479 ? 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:	0.101	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.295	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:	0.613	Fluc inhibitor:	0.283 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.716 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.584 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.109	Promiscuous compounds:	0.538

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.802	MDCK Permeability:	-4.982
Pgp-inhibitor:	0.0	Pgp-substrate:	0.759
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):	0.991
20% Bioavailability (F20%):	0.194	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.011
Plasma Protein Binding (PPB):	81.601%	Volume Distribution (VD):	-0.123
Fu:	17.526% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.246
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.095
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.372
HLM stability:	0.0 ? 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):

1.227

Half-life (T1/2):

5.337

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.942	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.074	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.994
Hematotoxicity:	0.228	Drug-induced Nephrotoxicity:	0.969
Genotoxicity:	0.959	RPMI-8226 Immunitoxicity:	0.356
A549 Cytotoxicity:	0.891	Hek293 Cytotoxicity:	0.46
BCF:	0.43 ? 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:	3.123 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.821 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.836 ? 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 NPC87655 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	18908
0.1-0.2	27420
0.2-0.3	2557
0.3-0.4	532
0.4-0.5	274
0.5-0.6	130
0.6-0.7	22
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8353	Intermediate Similarity	NPC150164
0.8	Intermediate Similarity	NPC289667
0.7647	Intermediate Similarity	NPC116458
0.7647	Intermediate Similarity	NPC246943
0.7586	Intermediate Similarity	NPC251417
0.7442	Intermediate Similarity	NPC605784
0.7204	Intermediate Similarity	NPC72016
0.7059	Intermediate Similarity	NPC297987
0.6966	Remote Similarity	NPC276377
0.6941	Remote Similarity	NPC249281
0.686	Remote Similarity	NPC136042
0.6818	Remote Similarity	NPC611303
0.6667	Remote Similarity	NPC35119
0.6632	Remote Similarity	NPC64425
0.6591	Remote Similarity	NPC46420
0.6505	Remote Similarity	NPC277532
0.65	Remote Similarity	NPC14187
0.6495	Remote Similarity	NPC32641
0.6495	Remote Similarity	NPC256188
0.6477	Remote Similarity	NPC64305
0.6408	Remote Similarity	NPC25523
0.6404	Remote Similarity	NPC84362
0.6404	Remote Similarity	NPC271692
0.6354	Remote Similarity	NPC186816
0.6292	Remote Similarity	NPC158674
0.625	Remote Similarity	NPC480441
0.6162	Remote Similarity	NPC606657
0.6154	Remote Similarity	NPC472459
0.6132	Remote Similarity	NPC470716
0.6095	Remote Similarity	NPC470715
0.5941	Remote Similarity	NPC5319
0.5934	Remote Similarity	NPC95090
0.5934	Remote Similarity	NPC27408
0.5872	Remote Similarity	NPC295625
0.58	Remote Similarity	NPC240306
0.5794	Remote Similarity	NPC164704
0.5745	Remote Similarity	NPC285197
0.5728	Remote Similarity	NPC76831
0.5714	Remote Similarity	NPC480466
0.5699	Remote Similarity	NPC24043
0.5684	Remote Similarity	NPC22832
0.5652	Remote Similarity	NPC77672
0.5652	Remote Similarity	NPC133671
0.5652	Remote Similarity	NPC135391
0.5652	Remote Similarity	NPC78263
0.5652	Remote Similarity	NPC250069
0.5612	Remote Similarity	NPC480463
0.5591	Remote Similarity	NPC277205
0.5591	Remote Similarity	NPC37919
0.5591	Remote Similarity	NPC189142
0.5591	Remote Similarity	NPC77660
0.5579	Remote Similarity	NPC60735
0.5579	Remote Similarity	NPC26230
0.5579	Remote Similarity	NPC488071
0.5575	Remote Similarity	NPC470720
0.5543	Remote Similarity	NPC111929
0.5543	Remote Similarity	NPC320283
0.5543	Remote Similarity	NPC41121
0.5543	Remote Similarity	NPC160515
0.5532	Remote Similarity	NPC27640
0.5521	Remote Similarity	NPC243930
0.5521	Remote Similarity	NPC120099
0.5521	Remote Similarity	NPC21666
0.5521	Remote Similarity	NPC486578
0.5514	Remote Similarity	NPC121703
0.5487	Remote Similarity	NPC470717
0.5484	Remote Similarity	NPC261866
0.5484	Remote Similarity	NPC39360
0.5484	Remote Similarity	NPC19709
0.5484	Remote Similarity	NPC29763
0.5484	Remote Similarity	NPC210003
0.5484	Remote Similarity	NPC238376
0.5472	Remote Similarity	NPC135358
0.5426	Remote Similarity	NPC145038
0.5426	Remote Similarity	NPC56077
0.5426	Remote Similarity	NPC281131
0.5426	Remote Similarity	NPC253662
0.5426	Remote Similarity	NPC179950
0.5426	Remote Similarity	NPC323593
0.5426	Remote Similarity	NPC88789
0.5426	Remote Similarity	NPC203500
0.5426	Remote Similarity	NPC234739
0.5426	Remote Similarity	NPC491374
0.5417	Remote Similarity	NPC219904
0.5376	Remote Similarity	NPC473043
0.5376	Remote Similarity	NPC331652
0.5368	Remote Similarity	NPC73511
0.5361	Remote Similarity	NPC148710
0.5351	Remote Similarity	NPC470719
0.5333	Remote Similarity	NPC142142
0.5319	Remote Similarity	NPC127546
0.5319	Remote Similarity	NPC19388
0.5319	Remote Similarity	NPC240431
0.5319	Remote Similarity	NPC57625
0.5319	Remote Similarity	NPC55786
0.5319	Remote Similarity	NPC108831
0.5319	Remote Similarity	NPC173637
0.5319	Remote Similarity	NPC317489
0.5319	Remote Similarity	NPC223424
0.5319	Remote Similarity	NPC182634
0.5319	Remote Similarity	NPC600591
0.5312	Remote Similarity	NPC59534
0.5306	Remote Similarity	NPC607707
0.5294	Remote Similarity	NPC22062
0.5294	Remote Similarity	NPC473634
0.5294	Remote Similarity	NPC138811
0.5288	Remote Similarity	NPC483414
0.5288	Remote Similarity	NPC65711
0.5259	Remote Similarity	NPC138990
0.5253	Remote Similarity	NPC488072
0.5213	Remote Similarity	NPC135599
0.5213	Remote Similarity	NPC73855
0.5213	Remote Similarity	NPC113968
0.5213	Remote Similarity	NPC328940
0.5213	Remote Similarity	NPC277174
0.5213	Remote Similarity	NPC606877
0.5208	Remote Similarity	NPC488080
0.5208	Remote Similarity	NPC349108
0.5208	Remote Similarity	NPC169977
0.5204	Remote Similarity	NPC601144
0.5204	Remote Similarity	NPC609478
0.52	Remote Similarity	NPC265115
0.5189	Remote Similarity	NPC486577
0.5164	Remote Similarity	NPC223860
0.5158	Remote Similarity	NPC58053
0.5155	Remote Similarity	NPC42773
0.5155	Remote Similarity	NPC45522
0.5155	Remote Similarity	NPC325555
0.5155	Remote Similarity	NPC226304
0.5155	Remote Similarity	NPC599850
0.5152	Remote Similarity	NPC311830
0.5149	Remote Similarity	NPC278419
0.5149	Remote Similarity	NPC179198
0.5143	Remote Similarity	NPC483415
0.514	Remote Similarity	NPC475382
0.5128	Remote Similarity	NPC209550
0.5104	Remote Similarity	NPC8573
0.5104	Remote Similarity	NPC197896
0.5104	Remote Similarity	NPC313163
0.5104	Remote Similarity	NPC265530
0.5102	Remote Similarity	NPC307938
0.51	Remote Similarity	NPC203050
0.51	Remote Similarity	NPC225434
0.51	Remote Similarity	NPC355481
0.5094	Remote Similarity	NPC483416
0.5094	Remote Similarity	NPC209296
0.5089	Remote Similarity	NPC470712
0.5085	Remote Similarity	NPC175429
0.5052	Remote Similarity	NPC186807
0.5052	Remote Similarity	NPC305811
0.5052	Remote Similarity	NPC181712
0.5052	Remote Similarity	NPC603655
0.5049	Remote Similarity	NPC173582
0.5049	Remote Similarity	NPC265885
0.5049	Remote Similarity	NPC181465
0.5049	Remote Similarity	NPC215710
0.5049	Remote Similarity	NPC275454
0.5049	Remote Similarity	NPC67105
0.5049	Remote Similarity	NPC473438
0.5049	Remote Similarity	NPC253788

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87655 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5043
0.1-0.2	4044
0.2-0.3	54
0.3-0.4	2
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
0.5941	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7808	Phase 3
0.5728	Remote Similarity	NPD7251	Phase 2
0.5094	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