NPASS Compound

Natural Product: NPC243930

Natural Product ID	NPC243930
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	URUMYDGZBWVMMP-DODNOZFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3325486
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 58 61 0 0 0 0 0 0 0 0999 V2000 -5.9990 0.7048 -3.3235 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5832 1.3529 -2.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8987 1.1073 -0.9378 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5814 1.5663 -1.0479 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9353 1.1023 0.1246 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5644 1.0689 0.0307 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6827 0.0325 0.0848 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0922 -1.2755 0.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1157 -2.2463 0.2606 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4933 -3.5883 0.3917 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2426 -1.9346 0.1792 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6511 -0.6256 0.0484 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3185 0.3512 0.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9416 -0.3022 -0.0312 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8976 -1.1972 0.0098 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -2.5172 0.1403 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2015 -2.9216 0.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8491 -4.1100 0.3459 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3143 -0.7715 -0.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6137 0.5637 -0.1985 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8845 1.0437 -0.2890 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9480 0.1496 -0.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6729 -1.1903 -0.1506 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3578 -1.6630 -0.0594 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7267 -2.1247 -0.1226 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4213 -3.4981 -0.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2494 0.6216 -0.3559 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4955 1.9921 -0.4718 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4406 2.0459 1.2171 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8896 1.6945 1.4641 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6382 1.8081 0.1533 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9149 1.2529 0.2433 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4624 2.5518 2.4094 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6812 1.9526 2.3789 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8174 -0.2458 -3.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6759 1.1108 -2.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5362 2.4520 -2.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9210 0.0123 -0.7258 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3248 0.0928 0.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1455 -1.5083 0.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8227 -3.8897 1.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0014 1.3909 -0.1021 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2874 -3.2792 0.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7533 1.2522 -0.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0244 2.1197 -0.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1945 -2.7092 0.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9291 -3.7667 0.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3399 -4.1267 -0.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7166 -3.8019 -0.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1866 2.4678 0.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8618 2.4938 -1.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5709 2.2305 -0.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4416 3.0941 0.7962 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9295 0.6422 1.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7055 2.8920 -0.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5524 1.8978 0.6708 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0903 3.4701 2.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6127 2.8296 2.8454 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 2 0 8 9 1 0 9 10 1 0 9 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 15 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 22 27 1 0 27 28 1 0 5 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 29 34 1 0 31 3 1 0 13 7 1 0 24 19 1 0 17 11 1 0 1 35 1 0 2 36 1 0 2 37 1 0 3 38 1 1 5 39 1 1 8 40 1 0 10 41 1 0 13 42 1 0 16 43 1 0 20 44 1 0 21 45 1 0 24 46 1 0 26 47 1 0 26 48 1 0 26 49 1 0 28 50 1 0 28 51 1 0 28 52 1 0 29 53 1 6 30 54 1 1 31 55 1 6 32 56 1 0 33 57 1 0 34 58 1 0 M END

Standard InCHIKey	URUMYDGZBWVMMP-DODNOZFWSA-N
Standard InCHI	InChI=1S/C23H24O11/c1-30-14-4-3-10(5-16(14)31-2)15-8-13(26)19-12(25)6-11(7-17(19)33-15)32-23-22(29)21(28)20(27)18(9-24)34-23/h3-8,18,20-25,27-29H,9H2,1-2H3/t18-,20-,21+,22-,23-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.13	Volume:	447.739 ? Van der Waals volume.
Dense:	1.063	LogP:	1.428 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.717 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.622 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	168.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.333	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.801	Fsp³:	0.348
MCE-18:	86.387 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.597	Fluc inhibitor:	0.35 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.962 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.915 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.094	Promiscuous compounds:	0.469

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.98	MDCK Permeability:	-5.169
Pgp-inhibitor:	0.012	Pgp-substrate:	0.543
PAMPA:	0.856 ? 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):	0.903
20% Bioavailability (F20%):	0.112	30% Bioavailability (F30%):	0.964
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.296
Plasma Protein Binding (PPB):	87.231%	Volume Distribution (VD):	-0.102
Fu:	12.576% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.969
BSEP inhibitor:	0.135

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.18
HLM stability:	0.007 ? 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):

2.964

Half-life (T1/2):

3.74

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.119
Human Hepatotoxicity (H-HT):	0.629	Drug-induced Liver Injury (DILI):	0.981
AMES Toxicity:	0.913	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.052	Skin Sensitization:	0.983
Carcinogencity:	0.487	Eye Corrosion:	0.0
Eye Irritation:	0.513	Respiratory Toxicity:	0.049
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.797
Hematotoxicity:	0.288	Drug-induced Nephrotoxicity:	0.539
Genotoxicity:	0.698	RPMI-8226 Immunitoxicity:	0.114
A549 Cytotoxicity:	0.22	Hek293 Cytotoxicity:	0.325
BCF:	0.408 ? 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:	3.097 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.478 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.72 ? 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
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[25127164]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25176187]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26696523]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12728	Artemisia rupestris	Species	Asteraceae	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell line	1

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	9510.0	nM	PMID[22871217]

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 NPC243930 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	21943
0.1-0.2	23768
0.2-0.3	2712
0.3-0.4	952
0.4-0.5	286
0.5-0.6	127
0.6-0.7	41
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9306	High Similarity	NPC607707
0.8611	High Similarity	NPC95090
0.8611	High Similarity	NPC27408
0.8158	Intermediate Similarity	NPC22832
0.8052	Intermediate Similarity	NPC311830
0.7792	Intermediate Similarity	NPC609451
0.7733	Intermediate Similarity	NPC39360
0.7733	Intermediate Similarity	NPC29763
0.7733	Intermediate Similarity	NPC210003
0.7692	Intermediate Similarity	NPC601144
0.7632	Intermediate Similarity	NPC189142
0.7632	Intermediate Similarity	NPC77660
0.7595	Intermediate Similarity	NPC88023
0.7595	Intermediate Similarity	NPC309025
0.75	Intermediate Similarity	NPC261866
0.7436	Intermediate Similarity	NPC182045
0.7308	Intermediate Similarity	NPC181712
0.7273	Intermediate Similarity	NPC58053
0.7089	Intermediate Similarity	NPC186807
0.6857	Remote Similarity	NPC195202
0.679	Remote Similarity	NPC27942
0.6627	Remote Similarity	NPC486578
0.6627	Remote Similarity	NPC605067
0.6625	Remote Similarity	NPC289667
0.6625	Remote Similarity	NPC143851
0.6548	Remote Similarity	NPC602805
0.6543	Remote Similarity	NPC93337
0.6506	Remote Similarity	NPC285197
0.65	Remote Similarity	NPC331652
0.6463	Remote Similarity	NPC84362
0.6463	Remote Similarity	NPC105025
0.6463	Remote Similarity	NPC45638
0.6429	Remote Similarity	NPC284960
0.6429	Remote Similarity	NPC80188
0.642	Remote Similarity	NPC19709
0.6413	Remote Similarity	NPC475382
0.6386	Remote Similarity	NPC201292
0.6353	Remote Similarity	NPC220169
0.6341	Remote Similarity	NPC277205
0.6341	Remote Similarity	NPC37919
0.6341	Remote Similarity	NPC323593
0.6341	Remote Similarity	NPC203500
0.6322	Remote Similarity	NPC8856
0.6296	Remote Similarity	NPC473043
0.6292	Remote Similarity	NPC22062
0.6292	Remote Similarity	NPC473634
0.6292	Remote Similarity	NPC138811
0.6279	Remote Similarity	NPC190003
0.6279	Remote Similarity	NPC601586
0.6237	Remote Similarity	NPC195257
0.622	Remote Similarity	NPC110349
0.6154	Remote Similarity	NPC46202
0.6145	Remote Similarity	NPC297987
0.6145	Remote Similarity	NPC136042
0.6118	Remote Similarity	NPC191306
0.6071	Remote Similarity	NPC610763
0.6047	Remote Similarity	NPC601710
0.6024	Remote Similarity	NPC45618
0.6022	Remote Similarity	NPC473623
0.6022	Remote Similarity	NPC209296
0.5957	Remote Similarity	NPC488089
0.5955	Remote Similarity	NPC251417
0.5952	Remote Similarity	NPC168822
0.5952	Remote Similarity	NPC146792
0.5949	Remote Similarity	NPC191154
0.5934	Remote Similarity	NPC65003
0.593	Remote Similarity	NPC307938
0.5882	Remote Similarity	NPC58716
0.5882	Remote Similarity	NPC73511
0.5875	Remote Similarity	NPC134819
0.587	Remote Similarity	NPC115674
0.5862	Remote Similarity	NPC608742
0.5814	Remote Similarity	NPC60966
0.5795	Remote Similarity	NPC116458
0.5795	Remote Similarity	NPC246943
0.5795	Remote Similarity	NPC605784
0.5765	Remote Similarity	NPC234739
0.5743	Remote Similarity	NPC311850
0.5686	Remote Similarity	NPC488083
0.5684	Remote Similarity	NPC124155
0.5652	Remote Similarity	NPC44931
0.5638	Remote Similarity	NPC64425
0.5638	Remote Similarity	NPC64051
0.5632	Remote Similarity	NPC222936
0.5625	Remote Similarity	NPC270675
0.5625	Remote Similarity	NPC195685
0.5616	Remote Similarity	NPC29353
0.56	Remote Similarity	NPC69394
0.5591	Remote Similarity	NPC210073
0.5581	Remote Similarity	NPC197896
0.5581	Remote Similarity	NPC313163
0.5579	Remote Similarity	NPC65711
0.5577	Remote Similarity	NPC68592
0.5568	Remote Similarity	NPC611303
0.5545	Remote Similarity	NPC472993
0.5543	Remote Similarity	NPC603300
0.5541	Remote Similarity	NPC33265
0.5526	Remote Similarity	NPC177298
0.5524	Remote Similarity	NPC198199
0.5521	Remote Similarity	NPC229409
0.5517	Remote Similarity	NPC22195
0.5517	Remote Similarity	NPC21190
0.551	Remote Similarity	NPC101636
0.5506	Remote Similarity	NPC21666
0.5495	Remote Similarity	NPC211594
0.5474	Remote Similarity	NPC284277
0.5474	Remote Similarity	NPC475366
0.5474	Remote Similarity	NPC475497
0.5465	Remote Similarity	NPC83283
0.5455	Remote Similarity	NPC472459
0.5455	Remote Similarity	NPC472994
0.5455	Remote Similarity	NPC135358
0.5455	Remote Similarity	NPC117260
0.5435	Remote Similarity	NPC606546
0.5393	Remote Similarity	NPC80140
0.537	Remote Similarity	NPC120952
0.5368	Remote Similarity	NPC122809
0.5361	Remote Similarity	NPC210961
0.5354	Remote Similarity	NPC298171
0.5341	Remote Similarity	NPC24043
0.5341	Remote Similarity	NPC603655
0.534	Remote Similarity	NPC470715
0.534	Remote Similarity	NPC164704
0.5326	Remote Similarity	NPC4390
0.5325	Remote Similarity	NPC283600
0.5325	Remote Similarity	NPC12200
0.5325	Remote Similarity	NPC223579
0.5319	Remote Similarity	NPC275454
0.53	Remote Similarity	NPC484301
0.53	Remote Similarity	NPC253685
0.5287	Remote Similarity	NPC44558
0.5287	Remote Similarity	NPC108831
0.5287	Remote Similarity	NPC238376
0.5287	Remote Similarity	NPC182634
0.5283	Remote Similarity	NPC295625
0.5273	Remote Similarity	NPC262222
0.5263	Remote Similarity	NPC607513
0.5256	Remote Similarity	NPC137062
0.5238	Remote Similarity	NPC470716
0.5234	Remote Similarity	NPC298666
0.5227	Remote Similarity	NPC64305
0.5227	Remote Similarity	NPC259152
0.5222	Remote Similarity	NPC282169
0.5222	Remote Similarity	NPC20505
0.5222	Remote Similarity	NPC488071
0.5217	Remote Similarity	NPC488072
0.5217	Remote Similarity	NPC267254
0.5208	Remote Similarity	NPC204693
0.5208	Remote Similarity	NPC131745
0.5204	Remote Similarity	NPC35119
0.52	Remote Similarity	NPC127447
0.5196	Remote Similarity	NPC11468
0.5195	Remote Similarity	NPC328119
0.5195	Remote Similarity	NPC166753
0.5185	Remote Similarity	NPC470719
0.5185	Remote Similarity	NPC470717
0.5169	Remote Similarity	NPC46420
0.5169	Remote Similarity	NPC271692
0.5169	Remote Similarity	NPC600680
0.5169	Remote Similarity	NPC602537
0.5165	Remote Similarity	NPC148710
0.5165	Remote Similarity	NPC120099
0.5165	Remote Similarity	NPC609478
0.5161	Remote Similarity	NPC172807
0.5143	Remote Similarity	NPC277532
0.5138	Remote Similarity	NPC470720
0.5132	Remote Similarity	NPC48479
0.5132	Remote Similarity	NPC234133
0.5128	Remote Similarity	NPC236769
0.5114	Remote Similarity	NPC210042
0.5114	Remote Similarity	NPC249281
0.5111	Remote Similarity	NPC21100
0.5106	Remote Similarity	NPC254540
0.51	Remote Similarity	NPC479765
0.5098	Remote Similarity	NPC14187
0.5065	Remote Similarity	NPC108406
0.5056	Remote Similarity	NPC158674
0.5055	Remote Similarity	NPC224462
0.5055	Remote Similarity	NPC479402
0.5054	Remote Similarity	NPC469931
0.5052	Remote Similarity	NPC257566
0.5051	Remote Similarity	NPC32641
0.5051	Remote Similarity	NPC256188
0.5051	Remote Similarity	NPC483707
0.5051	Remote Similarity	NPC150767
0.5048	Remote Similarity	NPC473644
0.5044	Remote Similarity	NPC35924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC243930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5188
0.1-0.2	3856
0.2-0.3	88
0.3-0.4	10
0.4-0.5	5
0.5-0.6	1
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
0.6022	Remote Similarity	NPD7054	Phase 4
0.5049	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