NPASS Compound

Natural Product: NPC12920

Natural Product ID	NPC12920
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FQKGNOGAGLOTLV-UKWZQOBBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	53317532
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 55 58 0 0 0 0 0 0 0 0999 V2000 -5.3818 2.3917 -2.0512 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9219 1.0233 -2.1174 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8052 0.6773 -1.3791 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5537 0.8636 -1.9998 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4968 1.3185 -3.1685 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3694 0.5634 -1.3700 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1581 0.7514 -1.9883 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0280 0.4456 -1.3421 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9774 -0.0510 -0.0673 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2716 -0.2352 0.5455 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4578 0.0629 -0.0811 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6062 -0.1044 0.4762 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7774 0.1784 -0.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9972 -0.0630 0.6379 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2619 -0.0491 0.1337 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3965 -0.2482 0.9299 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2429 -0.4681 2.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9793 -0.4901 2.8139 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8901 -0.2935 2.0214 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3358 -0.6749 3.1257 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1232 -0.3662 0.6074 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4485 -0.2678 0.2018 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1948 0.6357 1.1691 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6421 0.3013 1.1309 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0076 -0.3150 -0.1997 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2250 -1.5803 -0.4579 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0102 -2.8256 -0.1201 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2325 -2.8620 -0.7822 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9994 -1.5542 0.2138 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7562 0.5652 -1.2471 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0247 -0.5420 2.1547 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9606 1.9770 0.8023 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1104 1.2577 -3.2875 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6888 3.0130 -1.4712 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4949 2.8108 -3.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3564 2.3967 -1.5589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9657 0.6218 -1.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2745 -0.6307 1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4391 0.0877 -0.9054 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3590 -0.2263 0.4866 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8413 -0.6648 3.8815 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8878 -0.3113 2.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2747 -0.7372 2.7319 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5046 0.1313 -0.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7209 0.5029 2.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2527 1.2318 1.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0728 -0.5584 -0.1867 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9939 -1.6182 -1.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4278 -3.7027 -0.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2095 -2.9408 0.9572 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9935 -3.0149 -0.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4030 1.3100 -1.1930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3171 -1.1776 2.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5037 2.4834 1.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6350 1.9000 -3.5286 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 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 9 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 27 28 1 0 26 29 1 0 25 30 1 0 24 31 1 0 23 32 1 0 7 33 1 0 13 3 2 0 19 14 1 0 29 22 1 0 11 6 1 0 1 34 1 0 1 35 1 0 1 36 1 0 8 37 1 0 10 38 1 0 15 39 1 0 16 40 1 0 18 41 1 0 19 42 1 0 20 43 1 0 22 44 1 6 23 45 1 1 24 46 1 1 25 47 1 1 26 48 1 6 27 49 1 0 27 50 1 0 28 51 1 0 30 52 1 0 31 53 1 0 32 54 1 0 33 55 1 0 M END

Standard InCHIKey	FQKGNOGAGLOTLV-UKWZQOBBSA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-21-17(27)15-12(25)6-11(31-22-19(29)18(28)16(26)14(8-23)33-22)7-13(15)32-20(21)9-2-4-10(24)5-3-9/h2-7,14,16,18-19,22-26,28-29H,8H2,1H3/t14-,16-,18+,19-,22-/m1/s1
SMILES	COc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.12	Volume:	430.443 ? Van der Waals volume.
Dense:	1.074	LogP:	1.198 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.529 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.483 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	179.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.302	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.871	Fsp³:	0.318
MCE-18:	86.966 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.592	Fluc inhibitor:	0.297 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.935 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.872 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.099	Promiscuous compounds:	0.515

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.225	MDCK Permeability:	-5.174
Pgp-inhibitor:	0.005	Pgp-substrate:	0.461
PAMPA:	0.994 ? 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):	0.452
20% Bioavailability (F20%):	0.035	30% Bioavailability (F30%):	0.94
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.34
Plasma Protein Binding (PPB):	85.258%	Volume Distribution (VD):	-0.087
Fu:	13.228% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.973
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.762
BSEP inhibitor:	0.13

ADMET: Metabolism

CYP1A2-inhibitor:	0.017	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:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.904
HLM stability:	0.174 ? 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):

3.172

Half-life (T1/2):

3.458

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.119
Human Hepatotoxicity (H-HT):	0.611	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.874	Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.063	Skin Sensitization:	0.989
Carcinogencity:	0.439	Eye Corrosion:	0.0
Eye Irritation:	0.473	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.793
Hematotoxicity:	0.146	Drug-induced Nephrotoxicity:	0.35
Genotoxicity:	0.936	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.263	Hek293 Cytotoxicity:	0.479
BCF:	0.463 ? 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:	3.022 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.383 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.625 ? 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
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	whole plant	Gongshan County, Yunnan, China	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	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 NPC12920 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	23310
0.1-0.2	22243
0.2-0.3	2830
0.3-0.4	829
0.4-0.5	362
0.5-0.6	91
0.6-0.7	78
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC297987
0.8857	High Similarity	NPC84362
0.863	High Similarity	NPC116458
0.863	High Similarity	NPC246943
0.8194	Intermediate Similarity	NPC136042
0.8056	Intermediate Similarity	NPC289667
0.7838	Intermediate Similarity	NPC46420
0.7808	Intermediate Similarity	NPC249281
0.7778	Intermediate Similarity	NPC64425
0.7662	Intermediate Similarity	NPC605784
0.76	Intermediate Similarity	NPC24043
0.7568	Intermediate Similarity	NPC39360
0.7568	Intermediate Similarity	NPC29763
0.7568	Intermediate Similarity	NPC210003
0.7467	Intermediate Similarity	NPC323593
0.7467	Intermediate Similarity	NPC203500
0.7381	Intermediate Similarity	NPC35119
0.7333	Intermediate Similarity	NPC77672
0.7333	Intermediate Similarity	NPC133671
0.7333	Intermediate Similarity	NPC135391
0.7333	Intermediate Similarity	NPC78263
0.7333	Intermediate Similarity	NPC250069
0.7176	Intermediate Similarity	NPC32641
0.7176	Intermediate Similarity	NPC256188
0.7143	Intermediate Similarity	NPC488080
0.7143	Intermediate Similarity	NPC169977
0.7125	Intermediate Similarity	NPC276377
0.7013	Intermediate Similarity	NPC277205
0.7013	Intermediate Similarity	NPC37919
0.7013	Intermediate Similarity	NPC189142
0.7013	Intermediate Similarity	NPC77660
0.6962	Remote Similarity	NPC168584
0.6951	Remote Similarity	NPC251417
0.6941	Remote Similarity	NPC240306
0.6923	Remote Similarity	NPC271692
0.6905	Remote Similarity	NPC150164
0.6848	Remote Similarity	NPC25523
0.6848	Remote Similarity	NPC164704
0.6835	Remote Similarity	NPC472459
0.6795	Remote Similarity	NPC95090
0.6795	Remote Similarity	NPC27408
0.679	Remote Similarity	NPC311830
0.6771	Remote Similarity	NPC470717
0.675	Remote Similarity	NPC488071
0.6716	Remote Similarity	NPC146679
0.6701	Remote Similarity	NPC470720
0.6667	Remote Similarity	NPC22832
0.6667	Remote Similarity	NPC261866
0.6628	Remote Similarity	NPC186816
0.6582	Remote Similarity	NPC145038
0.6582	Remote Similarity	NPC8573
0.6582	Remote Similarity	NPC56077
0.6582	Remote Similarity	NPC281131
0.6582	Remote Similarity	NPC64305
0.6582	Remote Similarity	NPC253662
0.6582	Remote Similarity	NPC179950
0.6582	Remote Similarity	NPC88789
0.6582	Remote Similarity	NPC491374
0.6543	Remote Similarity	NPC307938
0.6543	Remote Similarity	NPC611303
0.6506	Remote Similarity	NPC203050
0.6506	Remote Similarity	NPC225434
0.6506	Remote Similarity	NPC601586
0.6494	Remote Similarity	NPC288084
0.6489	Remote Similarity	NPC470715
0.6463	Remote Similarity	NPC243930
0.6463	Remote Similarity	NPC21666
0.6463	Remote Similarity	NPC486578
0.6463	Remote Similarity	NPC601144
0.6463	Remote Similarity	NPC609478
0.642	Remote Similarity	NPC42773
0.642	Remote Similarity	NPC45522
0.642	Remote Similarity	NPC599850
0.6413	Remote Similarity	NPC14187
0.6404	Remote Similarity	NPC72016
0.6375	Remote Similarity	NPC93337
0.6375	Remote Similarity	NPC197896
0.6375	Remote Similarity	NPC313163
0.6375	Remote Similarity	NPC158674
0.6354	Remote Similarity	NPC470716
0.6344	Remote Similarity	NPC121703
0.6341	Remote Similarity	NPC285197
0.6329	Remote Similarity	NPC331652
0.631	Remote Similarity	NPC488072
0.6296	Remote Similarity	NPC105025
0.6296	Remote Similarity	NPC603655
0.6296	Remote Similarity	NPC610763
0.6265	Remote Similarity	NPC148710
0.6265	Remote Similarity	NPC120099
0.625	Remote Similarity	NPC108831
0.625	Remote Similarity	NPC277532
0.625	Remote Similarity	NPC182634
0.6224	Remote Similarity	NPC295625
0.622	Remote Similarity	NPC27942
0.622	Remote Similarity	NPC325555
0.622	Remote Similarity	NPC226304
0.619	Remote Similarity	NPC607707
0.6163	Remote Similarity	NPC473682
0.6146	Remote Similarity	NPC480441
0.6125	Remote Similarity	NPC111929
0.6125	Remote Similarity	NPC320283
0.6125	Remote Similarity	NPC41121
0.6092	Remote Similarity	NPC480466
0.6092	Remote Similarity	NPC139320
0.6071	Remote Similarity	NPC101026
0.6071	Remote Similarity	NPC488077
0.6049	Remote Similarity	NPC19388
0.6049	Remote Similarity	NPC240431
0.6049	Remote Similarity	NPC55786
0.5978	Remote Similarity	NPC142142
0.5976	Remote Similarity	NPC146792
0.5974	Remote Similarity	NPC191154
0.5952	Remote Similarity	NPC60735
0.5952	Remote Similarity	NPC26230
0.5952	Remote Similarity	NPC80140
0.5941	Remote Similarity	NPC470719
0.593	Remote Similarity	NPC170052
0.593	Remote Similarity	NPC135846
0.5904	Remote Similarity	NPC84265
0.5904	Remote Similarity	NPC45638
0.5854	Remote Similarity	NPC19709
0.5854	Remote Similarity	NPC238376
0.5833	Remote Similarity	NPC117260
0.5833	Remote Similarity	NPC201292
0.5814	Remote Similarity	NPC206123
0.5806	Remote Similarity	NPC486577
0.5802	Remote Similarity	NPC67037
0.5802	Remote Similarity	NPC255615
0.5775	Remote Similarity	NPC188871
0.5714	Remote Similarity	NPC22195
0.5714	Remote Similarity	NPC27640
0.5714	Remote Similarity	NPC21190
0.5714	Remote Similarity	NPC73511
0.5699	Remote Similarity	NPC606657
0.5696	Remote Similarity	NPC134819
0.5667	Remote Similarity	NPC470405
0.5663	Remote Similarity	NPC58053
0.5663	Remote Similarity	NPC83283
0.5634	Remote Similarity	NPC103904
0.5634	Remote Similarity	NPC262094
0.5618	Remote Similarity	NPC8856
0.5618	Remote Similarity	NPC480463
0.5604	Remote Similarity	NPC65003
0.5604	Remote Similarity	NPC156869
0.5595	Remote Similarity	NPC168822
0.5595	Remote Similarity	NPC234739
0.5556	Remote Similarity	NPC29958
0.5529	Remote Similarity	NPC245014
0.5529	Remote Similarity	NPC186807
0.5529	Remote Similarity	NPC58716
0.5529	Remote Similarity	NPC181712
0.5524	Remote Similarity	NPC138990
0.5495	Remote Similarity	NPC44931
0.5495	Remote Similarity	NPC471748
0.5495	Remote Similarity	NPC275454
0.5495	Remote Similarity	NPC163242
0.5495	Remote Similarity	NPC272068
0.5484	Remote Similarity	NPC488073
0.5476	Remote Similarity	NPC127546
0.5476	Remote Similarity	NPC57625
0.5476	Remote Similarity	NPC173637
0.5476	Remote Similarity	NPC317489
0.5476	Remote Similarity	NPC223424
0.5476	Remote Similarity	NPC600591
0.5474	Remote Similarity	NPC5319
0.5467	Remote Similarity	NPC78326
0.5465	Remote Similarity	NPC59534
0.5465	Remote Similarity	NPC100720
0.5465	Remote Similarity	NPC60966
0.5455	Remote Similarity	NPC223747
0.5455	Remote Similarity	NPC189564
0.5455	Remote Similarity	NPC602805
0.5435	Remote Similarity	NPC479405
0.5417	Remote Similarity	NPC76831
0.5412	Remote Similarity	NPC259152
0.5412	Remote Similarity	NPC609879
0.5402	Remote Similarity	NPC175107
0.5393	Remote Similarity	NPC469931
0.5393	Remote Similarity	NPC190003
0.5385	Remote Similarity	NPC471079
0.5376	Remote Similarity	NPC479404
0.5376	Remote Similarity	NPC470444
0.5366	Remote Similarity	NPC54802
0.5366	Remote Similarity	NPC197304
0.5357	Remote Similarity	NPC473043
0.5349	Remote Similarity	NPC305811
0.5347	Remote Similarity	NPC470712
0.5342	Remote Similarity	NPC101830
0.5341	Remote Similarity	NPC284960
0.5341	Remote Similarity	NPC224530
0.5341	Remote Similarity	NPC605067
0.5333	Remote Similarity	NPC254855
0.5333	Remote Similarity	NPC94610
0.5327	Remote Similarity	NPC175429
0.5326	Remote Similarity	NPC173582
0.5326	Remote Similarity	NPC265885
0.5326	Remote Similarity	NPC181465
0.5326	Remote Similarity	NPC215710
0.5326	Remote Similarity	NPC473438
0.5326	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 NPC12920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5598
0.1-0.2	3454
0.2-0.3	84
0.3-0.4	7
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
0.5579	Remote Similarity	NPD7251	Phase 2
0.5474	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5233	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.505	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