NPASS Compound

Natural Product: NPC36558

Natural Product ID	NPC36558
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NKFZLEYLWAFYEH-NSSLBSGISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21579174
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 70 74 0 0 0 0 0 0 0 0999 V2000 -2.4039 -0.4340 -2.4749 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8995 -0.2022 -3.7583 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2084 0.1778 -3.9393 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9800 0.3124 -2.8100 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4770 0.0809 -1.5538 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1405 -0.3090 -1.3362 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7069 -0.5012 0.0293 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4201 -0.5861 0.4244 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0602 -0.7859 1.7693 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1413 -0.8651 2.1083 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0545 -0.8912 2.6977 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7660 -1.0890 4.0551 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7677 -1.1933 4.9926 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0609 -1.0941 4.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3639 -0.9005 3.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3519 -0.7937 2.2490 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6438 -0.6100 0.9897 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1107 -1.1967 5.4656 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4460 -1.1827 4.4718 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3651 -0.4647 -0.4701 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2950 0.7742 -0.5424 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7642 0.6868 -0.7896 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3895 2.0350 -1.0589 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5326 2.8852 -1.9683 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1340 2.8929 -1.4065 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7720 3.8330 -2.1668 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0515 3.7999 -1.6325 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3446 1.5853 -1.4803 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5924 2.4014 -3.2575 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5835 1.8185 -1.7441 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4086 0.1274 0.2973 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1029 -1.0442 -0.0526 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5860 -0.9407 0.1993 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1995 -2.2277 0.7010 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3966 -2.9330 1.7392 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0633 -2.2443 1.8801 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5199 -2.1031 0.5967 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0621 -2.9986 2.9713 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4519 -1.9196 1.2388 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2991 -0.6305 -0.9828 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3056 0.6959 -2.9809 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7115 0.4113 -5.2173 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3853 -0.7444 -2.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2709 -0.3154 -4.6308 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0992 0.1928 -0.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6185 -1.3455 6.0504 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3805 -0.8200 2.8264 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0257 -1.4127 5.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1239 -1.7214 5.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0899 1.3086 0.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9204 0.0742 -1.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5788 2.6124 -0.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9387 3.9146 -1.9645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1946 3.1575 -0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3708 4.8615 -2.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7637 3.6405 -3.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0449 3.7863 -0.6604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8888 1.7754 -3.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7915 2.6313 -2.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9304 -1.1903 -1.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7726 -0.1363 0.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3895 -2.8610 -0.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2004 -3.9782 1.3615 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2819 -1.2147 2.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3770 -2.7732 2.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0524 -2.9678 2.8510 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1143 -1.7031 0.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0968 -0.0815 -0.7659 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5678 1.2658 -3.7570 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0770 -0.3317 -5.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 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 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 34 39 1 0 33 40 1 0 4 41 1 0 3 42 1 0 6 1 1 0 17 7 1 0 28 21 1 0 37 32 1 0 16 11 1 0 1 43 1 0 2 44 1 0 5 45 1 0 13 46 1 0 15 47 1 0 18 48 1 0 19 49 1 0 21 50 1 1 22 51 1 6 23 52 1 1 24 53 1 6 25 54 1 1 26 55 1 0 26 56 1 0 27 57 1 0 29 58 1 0 30 59 1 0 32 60 1 6 33 61 1 1 34 62 1 6 35 63 1 6 36 64 1 0 36 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 41 69 1 0 42 70 1 0 M END

Standard InCHIKey	NKFZLEYLWAFYEH-NSSLBSGISA-N
Standard InCHI	InChI=1S/C26H28O16/c27-6-15-18(34)20(36)24(42-25-21(37)17(33)13(32)7-38-25)26(40-15)41-23-19(35)16-12(31)4-9(28)5-14(16)39-22(23)8-1-2-10(29)11(30)3-8/h1-5,13,15,17-18,20-21,24-34,36-37H,6-7H2/t13-,15+,17-,18-,20-,21+,24+,25-,26-/m0/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.14	Volume:	535.022 ? Van der Waals volume.
Dense:	1.114	LogP:	0.683 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.946 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.838 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.73	Fsp³:	0.423
MCE-18:	120.378 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.639	Fluc inhibitor:	0.281 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.835 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.601 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.212	Promiscuous compounds:	0.717

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.534	MDCK Permeability:	-5.044
Pgp-inhibitor:	0.0	Pgp-substrate:	0.578
PAMPA:	0.997 ? 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):	0.946
20% Bioavailability (F20%):	0.988	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.662
Plasma Protein Binding (PPB):	80.698%	Volume Distribution (VD):	-0.166
Fu:	16.661% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.911
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.257
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.01	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.596
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.057
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.972 ? 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):

1.912

Half-life (T1/2):

3.048

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.107
Human Hepatotoxicity (H-HT):	0.614	Drug-induced Liver Injury (DILI):	0.947
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.067	Skin Sensitization:	1.0
Carcinogencity:	0.217	Eye Corrosion:	0.0
Eye Irritation:	0.919	Respiratory Toxicity:	0.062
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.919
Hematotoxicity:	0.199	Drug-induced Nephrotoxicity:	0.279
Genotoxicity:	0.974	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.994	Hek293 Cytotoxicity:	0.842
BCF:	0.459 ? 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:	3.036 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.588 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.743 ? 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
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075762]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24433009]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28032759]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14417	Iris tectorum	Species	Iridaceae	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 NPC36558 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	23020
0.1-0.2	22818
0.2-0.3	3164
0.3-0.4	454
0.4-0.5	188
0.5-0.6	105
0.6-0.7	69
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC255157
1.0	High Similarity	NPC259896
0.9125	High Similarity	NPC304741
0.8625	High Similarity	NPC254855
0.8625	High Similarity	NPC94610
0.8214	Intermediate Similarity	NPC155877
0.8068	Intermediate Similarity	NPC76831
0.7978	Intermediate Similarity	NPC292929
0.7935	Intermediate Similarity	NPC219043
0.7831	Intermediate Similarity	NPC170052
0.7831	Intermediate Similarity	NPC135846
0.7553	Intermediate Similarity	NPC48984
0.7471	Intermediate Similarity	NPC470405
0.7471	Intermediate Similarity	NPC163242
0.7471	Intermediate Similarity	NPC272068
0.7447	Intermediate Similarity	NPC488075
0.7326	Intermediate Similarity	NPC95866
0.7253	Intermediate Similarity	NPC122467
0.7204	Intermediate Similarity	NPC221342
0.7204	Intermediate Similarity	NPC476470
0.7079	Intermediate Similarity	NPC67326
0.7037	Intermediate Similarity	NPC276222
0.7037	Intermediate Similarity	NPC274618
0.7037	Intermediate Similarity	NPC118284
0.7037	Intermediate Similarity	NPC608147
0.7	Intermediate Similarity	NPC156869
0.6977	Remote Similarity	NPC224530
0.6947	Remote Similarity	NPC602448
0.6939	Remote Similarity	NPC303694
0.6915	Remote Similarity	NPC220173
0.6905	Remote Similarity	NPC145038
0.6905	Remote Similarity	NPC56077
0.6905	Remote Similarity	NPC281131
0.6905	Remote Similarity	NPC253662
0.6905	Remote Similarity	NPC179950
0.6905	Remote Similarity	NPC88789
0.6905	Remote Similarity	NPC491374
0.6848	Remote Similarity	NPC253521
0.6848	Remote Similarity	NPC113836
0.6827	Remote Similarity	NPC192539
0.6747	Remote Similarity	NPC67037
0.6747	Remote Similarity	NPC255615
0.6737	Remote Similarity	NPC89127
0.6636	Remote Similarity	NPC21359
0.6636	Remote Similarity	NPC460984
0.6629	Remote Similarity	NPC476215
0.6596	Remote Similarity	NPC12013
0.6596	Remote Similarity	NPC480471
0.6596	Remote Similarity	NPC11432
0.6596	Remote Similarity	NPC488076
0.6596	Remote Similarity	NPC477613
0.6593	Remote Similarity	NPC29958
0.6522	Remote Similarity	NPC471748
0.6413	Remote Similarity	NPC471079
0.6316	Remote Similarity	NPC61904
0.631	Remote Similarity	NPC54802
0.631	Remote Similarity	NPC197304
0.6277	Remote Similarity	NPC203259
0.6277	Remote Similarity	NPC33054
0.6277	Remote Similarity	NPC176740
0.6277	Remote Similarity	NPC471725
0.6277	Remote Similarity	NPC134532
0.6277	Remote Similarity	NPC602582
0.6207	Remote Similarity	NPC127546
0.6207	Remote Similarity	NPC57625
0.6207	Remote Similarity	NPC77672
0.6207	Remote Similarity	NPC133671
0.6207	Remote Similarity	NPC135391
0.6207	Remote Similarity	NPC173637
0.6207	Remote Similarity	NPC78263
0.6207	Remote Similarity	NPC317489
0.6207	Remote Similarity	NPC250069
0.6207	Remote Similarity	NPC223424
0.6207	Remote Similarity	NPC600591
0.6168	Remote Similarity	NPC480444
0.6139	Remote Similarity	NPC89052
0.6111	Remote Similarity	NPC175107
0.6105	Remote Similarity	NPC605592
0.6091	Remote Similarity	NPC25946
0.6075	Remote Similarity	NPC488740
0.6075	Remote Similarity	NPC488736
0.6075	Remote Similarity	NPC488733
0.6061	Remote Similarity	NPC473071
0.6047	Remote Similarity	NPC288084
0.6042	Remote Similarity	NPC470444
0.6042	Remote Similarity	NPC144097
0.604	Remote Similarity	NPC14187
0.6023	Remote Similarity	NPC19388
0.6023	Remote Similarity	NPC240431
0.6023	Remote Similarity	NPC55786
0.6022	Remote Similarity	NPC116864
0.6022	Remote Similarity	NPC244776
0.6019	Remote Similarity	NPC292019
0.6019	Remote Similarity	NPC202908
0.6	Remote Similarity	NPC216496
0.5982	Remote Similarity	NPC487499
0.5979	Remote Similarity	NPC240306
0.5978	Remote Similarity	NPC136761
0.5963	Remote Similarity	NPC488737
0.5962	Remote Similarity	NPC480441
0.5957	Remote Similarity	NPC473682
0.5955	Remote Similarity	NPC64305
0.5934	Remote Similarity	NPC60735
0.5934	Remote Similarity	NPC26230
0.5926	Remote Similarity	NPC162394
0.5895	Remote Similarity	NPC139320
0.5876	Remote Similarity	NPC35167
0.587	Remote Similarity	NPC120099
0.5862	Remote Similarity	NPC34531
0.5859	Remote Similarity	NPC32641
0.5859	Remote Similarity	NPC256188
0.5859	Remote Similarity	NPC35119
0.5849	Remote Similarity	NPC470718
0.5824	Remote Similarity	NPC472459
0.5816	Remote Similarity	NPC488074
0.581	Remote Similarity	NPC470712
0.58	Remote Similarity	NPC97119
0.5789	Remote Similarity	NPC275977
0.5776	Remote Similarity	NPC487502
0.5745	Remote Similarity	NPC203050
0.5745	Remote Similarity	NPC225434
0.5743	Remote Similarity	NPC471669
0.5738	Remote Similarity	NPC33083
0.5726	Remote Similarity	NPC249560
0.5714	Remote Similarity	NPC173837
0.5699	Remote Similarity	NPC259957
0.5699	Remote Similarity	NPC609478
0.5688	Remote Similarity	NPC480445
0.5673	Remote Similarity	NPC203145
0.567	Remote Similarity	NPC173582
0.567	Remote Similarity	NPC265885
0.567	Remote Similarity	NPC181465
0.567	Remote Similarity	NPC215710
0.567	Remote Similarity	NPC473438
0.567	Remote Similarity	NPC253788
0.5657	Remote Similarity	NPC488073
0.5625	Remote Similarity	NPC8856
0.5596	Remote Similarity	NPC488734
0.5596	Remote Similarity	NPC488735
0.5596	Remote Similarity	NPC488739
0.5596	Remote Similarity	NPC488732
0.5596	Remote Similarity	NPC488738
0.5591	Remote Similarity	NPC235260
0.5591	Remote Similarity	NPC155763
0.5583	Remote Similarity	NPC487500
0.5556	Remote Similarity	NPC111929
0.5556	Remote Similarity	NPC320283
0.5556	Remote Similarity	NPC41121
0.5545	Remote Similarity	NPC470713
0.5543	Remote Similarity	NPC52550
0.5537	Remote Similarity	NPC487501
0.5532	Remote Similarity	NPC484158
0.5514	Remote Similarity	NPC25523
0.551	Remote Similarity	NPC39834
0.55	Remote Similarity	NPC64425
0.5484	Remote Similarity	NPC42773
0.5484	Remote Similarity	NPC45522
0.5484	Remote Similarity	NPC325555
0.5484	Remote Similarity	NPC226304
0.5472	Remote Similarity	NPC189564
0.5446	Remote Similarity	NPC245452
0.5439	Remote Similarity	NPC480472
0.5435	Remote Similarity	NPC136042
0.5424	Remote Similarity	NPC30011
0.54	Remote Similarity	NPC115674
0.5392	Remote Similarity	NPC37668
0.5392	Remote Similarity	NPC473327
0.5385	Remote Similarity	NPC135599
0.5385	Remote Similarity	NPC73855
0.5385	Remote Similarity	NPC113968
0.5385	Remote Similarity	NPC328940
0.5385	Remote Similarity	NPC277174
0.5385	Remote Similarity	NPC606877
0.5375	Remote Similarity	NPC286342
0.5347	Remote Similarity	NPC154741
0.534	Remote Similarity	NPC142142
0.534	Remote Similarity	NPC603079
0.5333	Remote Similarity	NPC223426
0.5319	Remote Similarity	NPC599850
0.53	Remote Similarity	NPC473862
0.5294	Remote Similarity	NPC297503
0.5288	Remote Similarity	NPC476472
0.5288	Remote Similarity	NPC294815
0.5288	Remote Similarity	NPC16194
0.5283	Remote Similarity	NPC81042
0.5263	Remote Similarity	NPC159579
0.5263	Remote Similarity	NPC219904
0.5263	Remote Similarity	NPC48093
0.5254	Remote Similarity	NPC473554
0.5253	Remote Similarity	NPC258044
0.5253	Remote Similarity	NPC217387
0.5221	Remote Similarity	NPC156785
0.5217	Remote Similarity	NPC476771
0.5213	Remote Similarity	NPC84362
0.5189	Remote Similarity	NPC218161
0.5189	Remote Similarity	NPC253685
0.5161	Remote Similarity	NPC104677
0.5155	Remote Similarity	NPC223747
0.5155	Remote Similarity	NPC605784
0.5143	Remote Similarity	NPC135831

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC36558 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5892
0.1-0.2	3205
0.2-0.3	41
0.3-0.4	7
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6277	Remote Similarity	NPD6797	Phase 2

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