NPASS Compound

Natural Product: NPC140755

Natural Product ID	NPC140755
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AGCLBJVRDRUCIP-QKLVYGQBSA-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

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 73 77 0 0 0 0 0 0 0 0999 V2000 7.7946 1.4134 -0.7641 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1153 0.1432 -1.1318 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9083 -1.0971 -0.7503 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0493 -1.0513 0.7496 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8464 -0.5752 1.4598 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6377 -0.3175 0.6226 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8257 0.6666 1.1752 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5898 0.2828 1.5788 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6925 -0.2333 0.5138 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3856 0.8072 -0.5522 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1033 -0.0143 -1.8037 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2673 -1.1725 -1.3508 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5611 -0.9291 -0.0218 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4497 -0.0214 -0.1599 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8063 -0.0673 -0.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5608 1.1036 -0.2583 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9203 1.1431 -0.1513 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6618 0.0106 0.1943 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9454 -1.1320 0.4169 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5507 -1.1628 0.3046 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9667 -2.3800 0.5572 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1051 0.0878 0.2989 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9555 -0.9273 0.6279 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3400 -0.7406 0.7000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1382 -1.6492 0.9977 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8186 0.5143 0.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1540 0.7638 0.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6539 2.0259 0.2021 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7896 3.0480 -0.1299 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4456 2.7637 -0.1740 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9289 1.5221 0.0944 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6569 1.2785 0.0463 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2848 4.3106 -0.4054 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0341 -0.2661 0.8124 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5081 -2.1999 0.9102 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4582 -0.6218 1.0089 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8910 -2.4026 -1.4177 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4954 0.7526 -2.7895 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3447 1.7641 -0.7095 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8494 -0.0220 -0.6809 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5385 -1.5319 2.4592 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1497 -0.2014 1.0122 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0850 -2.1999 -1.0424 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8988 1.2388 -0.8368 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5462 1.8325 0.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5705 2.1867 -1.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0716 0.1151 -2.2612 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8828 -1.1493 -1.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3957 -2.0644 1.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0784 0.3512 2.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0465 -1.2726 0.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6407 -0.5188 2.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1363 1.1549 2.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1435 -1.1392 0.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4303 1.3463 -0.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0859 -0.4189 -2.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4187 -1.2361 -2.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1616 -1.9258 0.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0143 1.9818 -0.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4936 2.0486 -0.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4334 -2.0629 0.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -3.1861 -0.0334 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7162 2.2136 0.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7690 3.5738 -0.4364 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6681 4.8615 0.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0682 -0.5156 1.8017 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6485 -2.9766 0.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5478 -2.9402 -0.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8786 0.2591 -3.3599 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8606 1.6825 -1.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0743 -1.3481 3.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9415 -0.6818 0.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2131 -2.8948 -0.3293 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 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 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 2 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 29 33 1 0 27 34 1 0 23 35 1 0 13 36 1 0 12 37 1 0 11 38 1 0 10 39 1 0 6 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 40 2 1 0 36 9 1 0 20 15 1 0 32 22 1 0 31 26 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 6 4 49 1 1 5 50 1 1 6 51 1 6 8 52 1 0 8 53 1 0 9 54 1 6 10 55 1 1 11 56 1 6 12 57 1 6 13 58 1 1 16 59 1 0 17 60 1 0 19 61 1 0 21 62 1 0 28 63 1 0 30 64 1 0 33 65 1 0 34 66 1 0 35 67 1 0 37 68 1 0 38 69 1 0 39 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	AGCLBJVRDRUCIP-QKLVYGQBSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-17(31)20(34)23(37)26(40-8)39-7-15-18(32)21(35)24(38)27(43-15)42-13-3-2-9(4-11(13)29)25-22(36)19(33)16-12(30)5-10(28)6-14(16)41-25/h2-6,8,15,17-18,20-21,23-24,26-32,34-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,23-,24+,26-,27+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3ccc(cc3O)c3c(c(=O)c4c(cc(cc4o3)O)O)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	0.538 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.141 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.603 ? 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:	0.149	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.801	Fsp³:	0.444
MCE-18:	122.949 ? 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:	0
Colloidal aggregators:	0.64	Fluc inhibitor:	0.32 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.822 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.639 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.154	Promiscuous compounds:	0.601

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.58	MDCK Permeability:	-4.978
Pgp-inhibitor:	0.0	Pgp-substrate:	0.659
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):	0.867
20% Bioavailability (F20%):	0.114	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.107
Plasma Protein Binding (PPB):	85.411%	Volume Distribution (VD):	-0.145
Fu:	15.065% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.932
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	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:	1.0
HLM stability:	0.699 ? 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):

1.538

Half-life (T1/2):

4.656

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.149
Human Hepatotoxicity (H-HT):	0.333	Drug-induced Liver Injury (DILI):	0.94
AMES Toxicity:	0.85	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.072	Skin Sensitization:	0.946
Carcinogencity:	0.053	Eye Corrosion:	0.0
Eye Irritation:	0.689	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.854
Hematotoxicity:	0.043	Drug-induced Nephrotoxicity:	0.256
Genotoxicity:	0.826	RPMI-8226 Immunitoxicity:	0.168
A549 Cytotoxicity:	0.408	Hek293 Cytotoxicity:	0.459
BCF:	0.498 ? 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:	3.034 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.47 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.749 ? 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 NPC140755 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	16238
0.1-0.2	29354
0.2-0.3	3250
0.3-0.4	583
0.4-0.5	278
0.5-0.6	102
0.6-0.7	23
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8642	High Similarity	NPC187379
0.7841	Intermediate Similarity	NPC473327
0.7349	Intermediate Similarity	NPC21100
0.7079	Intermediate Similarity	NPC173582
0.7079	Intermediate Similarity	NPC265885
0.7079	Intermediate Similarity	NPC181465
0.7079	Intermediate Similarity	NPC215710
0.7079	Intermediate Similarity	NPC473438
0.7079	Intermediate Similarity	NPC253788
0.7021	Intermediate Similarity	NPC287889
0.7	Intermediate Similarity	NPC203259
0.7	Intermediate Similarity	NPC33054
0.7	Intermediate Similarity	NPC176740
0.7	Intermediate Similarity	NPC471725
0.7	Intermediate Similarity	NPC134532
0.7	Intermediate Similarity	NPC602582
0.6988	Remote Similarity	NPC254306
0.6915	Remote Similarity	NPC476472
0.6915	Remote Similarity	NPC294815
0.6915	Remote Similarity	NPC16194
0.6889	Remote Similarity	NPC39834
0.6889	Remote Similarity	NPC67105
0.6703	Remote Similarity	NPC227508
0.6354	Remote Similarity	NPC209296
0.6292	Remote Similarity	NPC219904
0.625	Remote Similarity	NPC12013
0.625	Remote Similarity	NPC11432
0.625	Remote Similarity	NPC477613
0.6224	Remote Similarity	NPC89127
0.6186	Remote Similarity	NPC122467
0.6176	Remote Similarity	NPC173837
0.6139	Remote Similarity	NPC89052
0.6105	Remote Similarity	NPC156869
0.6064	Remote Similarity	NPC471079
0.6055	Remote Similarity	NPC192539
0.6044	Remote Similarity	NPC197285
0.6	Remote Similarity	NPC67326
0.6	Remote Similarity	NPC221342
0.6	Remote Similarity	NPC476470
0.5941	Remote Similarity	NPC602448
0.5934	Remote Similarity	NPC191306
0.5934	Remote Similarity	NPC60735
0.5934	Remote Similarity	NPC26230
0.5934	Remote Similarity	NPC285197
0.5876	Remote Similarity	NPC473571
0.5876	Remote Similarity	NPC110941
0.587	Remote Similarity	NPC486578
0.587	Remote Similarity	NPC609478
0.5851	Remote Similarity	NPC116864
0.5851	Remote Similarity	NPC244776
0.5833	Remote Similarity	NPC275454
0.5816	Remote Similarity	NPC126784
0.5816	Remote Similarity	NPC241423
0.5816	Remote Similarity	NPC153755
0.5784	Remote Similarity	NPC135358
0.5773	Remote Similarity	NPC22062
0.5773	Remote Similarity	NPC65563
0.5773	Remote Similarity	NPC473634
0.5773	Remote Similarity	NPC470949
0.5773	Remote Similarity	NPC138811
0.5769	Remote Similarity	NPC189564
0.5729	Remote Similarity	NPC609888
0.5714	Remote Similarity	NPC292019
0.5714	Remote Similarity	NPC202908
0.5714	Remote Similarity	NPC186816
0.5684	Remote Similarity	NPC477848
0.5673	Remote Similarity	NPC203145
0.567	Remote Similarity	NPC44931
0.566	Remote Similarity	NPC303694
0.5638	Remote Similarity	NPC136761
0.5636	Remote Similarity	NPC162394
0.5625	Remote Similarity	NPC54394
0.5612	Remote Similarity	NPC210073
0.5604	Remote Similarity	NPC265530
0.5556	Remote Similarity	NPC111929
0.5556	Remote Similarity	NPC320283
0.5556	Remote Similarity	NPC204693
0.5556	Remote Similarity	NPC41121
0.5532	Remote Similarity	NPC120099
0.5517	Remote Similarity	NPC473554
0.5495	Remote Similarity	NPC127546
0.5495	Remote Similarity	NPC57625
0.5495	Remote Similarity	NPC108831
0.5495	Remote Similarity	NPC173637
0.5495	Remote Similarity	NPC317489
0.5495	Remote Similarity	NPC238376
0.5495	Remote Similarity	NPC223424
0.5495	Remote Similarity	NPC182634
0.5495	Remote Similarity	NPC600591
0.5474	Remote Similarity	NPC223747
0.5446	Remote Similarity	NPC470443
0.5398	Remote Similarity	NPC241781
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
0.5326	Remote Similarity	NPC476405
0.53	Remote Similarity	NPC303913
0.5288	Remote Similarity	NPC85751
0.5288	Remote Similarity	NPC471669
0.5288	Remote Similarity	NPC19240
0.5288	Remote Similarity	NPC477629
0.5278	Remote Similarity	NPC477895
0.5258	Remote Similarity	NPC476215
0.5248	Remote Similarity	NPC129264
0.5238	Remote Similarity	NPC292929
0.5221	Remote Similarity	NPC156785
0.5221	Remote Similarity	NPC474522
0.5208	Remote Similarity	NPC181616
0.5204	Remote Similarity	NPC95866
0.5196	Remote Similarity	NPC475366
0.5189	Remote Similarity	NPC223426
0.5169	Remote Similarity	NPC487499
0.5149	Remote Similarity	NPC233994
0.5149	Remote Similarity	NPC605592
0.5143	Remote Similarity	NPC80068
0.5143	Remote Similarity	NPC473073
0.514	Remote Similarity	NPC244875
0.514	Remote Similarity	NPC214621
0.514	Remote Similarity	NPC34267
0.514	Remote Similarity	NPC81042
0.5133	Remote Similarity	NPC198199
0.5133	Remote Similarity	NPC480445
0.5124	Remote Similarity	NPC487502
0.5106	Remote Similarity	NPC64305
0.5096	Remote Similarity	NPC37668
0.5096	Remote Similarity	NPC270448
0.5091	Remote Similarity	NPC217520
0.5091	Remote Similarity	NPC25523
0.5081	Remote Similarity	NPC487500
0.5051	Remote Similarity	NPC4390
0.505	Remote Similarity	NPC163242
0.505	Remote Similarity	NPC272068
0.5049	Remote Similarity	NPC470125
0.5049	Remote Similarity	NPC488073
0.5049	Remote Similarity	NPC488074
0.5048	Remote Similarity	NPC142142
0.5043	Remote Similarity	NPC480444
0.504	Remote Similarity	NPC487501

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC140755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4794
0.1-0.2	4288
0.2-0.3	55
0.3-0.4	6
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
0.7-0.8	1
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
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6354	Remote Similarity	NPD7054	Phase 4
0.5673	Remote Similarity	NPD7472	Pre-clinical
0.5524	Remote Similarity	NPD7808	Phase 3
0.5288	Remote Similarity	NPD7251	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