NPASS Compound

Natural Product: NPC243420

Natural Product ID	NPC243420
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PMDYNLFGCCRGRX-HMQYECKYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10463123
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 96105 0 0 0 0 0 0 0 0999 V2000 4.4448 1.4192 2.8065 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2991 2.1609 3.9616 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5644 1.6102 5.1806 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9829 0.2893 5.2257 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1271 -0.4486 4.0643 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8614 0.0988 2.8275 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0119 -0.6923 1.5506 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3325 -0.3291 0.9798 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2935 0.6818 -0.1101 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1380 0.5781 -1.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1796 1.0504 -2.3255 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0878 0.9468 -3.1658 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9169 0.3649 -2.7254 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8784 -0.1014 -1.4373 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6529 -0.7419 -0.8839 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5684 0.1890 -0.6515 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7782 1.4772 -0.2555 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2955 2.3289 -0.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5885 1.8898 -0.1643 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8285 0.5935 -0.5634 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2411 0.0951 -0.7336 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7575 -0.6004 0.4557 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8944 -1.9544 0.5283 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3906 -2.5670 1.6873 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7419 -1.7813 2.7593 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6088 -0.4177 2.6951 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1194 0.1751 1.5498 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9696 1.5420 1.4335 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9633 2.2571 0.2148 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9349 3.3686 0.1757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9142 4.3149 1.1945 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7817 5.3636 1.2072 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7181 5.5393 0.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7570 4.6139 -0.8021 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8787 3.5598 -0.8070 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6155 6.6147 0.2213 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1844 1.3002 -0.9307 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4680 0.7468 -0.8431 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6341 2.7722 0.0883 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2299 -2.4298 3.8906 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5660 -2.8037 -0.5079 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7470 -0.2327 -0.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9348 -1.5409 -1.2077 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0539 -2.0736 -2.1727 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4050 -3.4937 -2.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7056 -4.3881 -1.4856 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0209 -5.6877 -1.8410 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0416 -6.1104 -3.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7410 -5.2123 -4.1422 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4276 -3.9193 -3.7887 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3719 -7.4409 -3.4169 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3585 -1.9465 -1.7231 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7088 -3.1436 -1.0676 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0773 1.9834 -0.0819 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9794 -0.0060 -0.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9030 -0.4825 0.7180 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7926 0.2307 -3.5113 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3564 1.6282 -2.7505 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9307 -1.4990 0.4765 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4124 2.3706 6.3338 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2203 1.9101 1.8766 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9646 3.2074 3.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1992 -0.1651 6.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4528 -1.4632 4.1542 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9587 -1.7582 1.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0512 0.0262 1.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2646 1.7021 0.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2636 0.6961 -0.6869 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1880 1.3364 -4.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9200 -1.1796 0.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0735 3.3382 0.2999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2674 -0.4919 -1.6530 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4936 -3.6403 1.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8863 0.1909 3.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1832 4.2040 1.9960 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7521 6.0969 2.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5035 4.7624 -1.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9423 2.8634 -1.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5215 7.3602 0.8877 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9472 1.7389 -1.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6530 0.3050 -1.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0098 -3.0673 3.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5918 -2.5142 -1.4861 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2522 -1.5276 -3.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6839 -4.0424 -0.4685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2604 -6.4038 -1.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7517 -5.5210 -5.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1867 -3.1946 -4.5596 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7127 -8.0517 -3.8964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0039 -1.9429 -2.6462 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1700 -2.9134 -0.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2478 2.8060 0.4848 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0494 0.9080 -3.5623 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0298 1.0430 -3.2271 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2311 -2.1031 1.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3519 3.3752 6.2592 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 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 1 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 29 37 1 0 37 38 1 0 29 39 1 0 25 40 1 0 23 41 1 0 20 42 2 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 48 51 1 0 44 52 1 0 52 53 1 0 17 54 1 0 14 55 2 0 55 56 1 0 13 57 1 0 11 58 1 0 8 59 1 0 3 60 1 0 6 1 1 0 56 7 1 0 55 10 1 0 52 15 1 0 42 16 1 0 50 45 1 0 39 19 1 0 37 21 1 0 27 22 1 0 35 30 1 0 1 61 1 0 2 62 1 0 4 63 1 0 5 64 1 0 7 65 1 1 8 66 1 1 9 67 1 0 9 68 1 0 12 69 1 0 15 70 1 1 18 71 1 0 21 72 1 6 24 73 1 0 26 74 1 0 31 75 1 0 32 76 1 0 34 77 1 0 35 78 1 0 36 79 1 0 37 80 1 6 38 81 1 0 40 82 1 0 41 83 1 0 44 84 1 6 46 85 1 0 47 86 1 0 49 87 1 0 50 88 1 0 51 89 1 0 52 90 1 6 53 91 1 0 54 92 1 0 57 93 1 0 58 94 1 0 59 95 1 0 60 96 1 0 M END

Standard InCHIKey	PMDYNLFGCCRGRX-HMQYECKYSA-N
Standard InCHI	InChI=1S/C45H36O15/c46-21-7-1-18(2-8-21)40-30(54)15-25-26(50)16-28(52)34(42(25)57-40)37-35-29(53)17-32-36(43(35)58-41(39(37)55)19-3-9-22(47)10-4-19)38-33-27(51)13-24(49)14-31(33)59-45(60-32,44(38)56)20-5-11-23(48)12-6-20/h1-14,16-17,30,37-41,44,46-56H,15H2/t30-,37-,38+,39+,40+,41+,44+,45-/m0/s1
SMILES	c1cc(ccc1[C@@H]1[C@H](Cc2c(cc(c([C@H]3c4c(cc5c([C@H]6c7c(cc(cc7O[C@](c7ccc(cc7)O)([C@@H]6O)O5)O)O)c4O[C@H](c4ccc(cc4)O)[C@@H]3O)O)c2O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	816.21	Volume:	785.708 ? Van der Waals volume.
Dense:	1.039	LogP:	2.448 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.428 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.664 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	54.0
TPSA:	259.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	11.0	Rings:	10.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.073	Fsp³:	0.2
MCE-18:	200.0 ? 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:	0.969	Fluc inhibitor:	0.073 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.56 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.846 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.555	Promiscuous compounds:	0.081

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.284	MDCK Permeability:	-4.876
Pgp-inhibitor:	0.0	Pgp-substrate:	0.995
PAMPA:	0.005 ? 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):	0.0
20% Bioavailability (F20%):	0.256	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.979
Plasma Protein Binding (PPB):	93.861%	Volume Distribution (VD):	0.552
Fu:	8.613% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.375
BSEP inhibitor:	0.918

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

3.324

Half-life (T1/2):

5.559

ADMET: Toxicity

hERG Blockers:	0.16	hERG Blockers (10um):	0.718
Human Hepatotoxicity (H-HT):	0.988	Drug-induced Liver Injury (DILI):	0.565
AMES Toxicity:	0.227	Rat Oral Acute Toxicity:	0.627
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	0.996
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.431	Respiratory Toxicity:	0.941
Drug-induced Neurotoxicity:	0.219	Ototoxicity:	0.984
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.78
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.349
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.999
BCF:	1.191 ? 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:	4.086 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.953 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.517 ? 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
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8254348]
NPO20671	Selliguea feei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20671	Selliguea feei	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 NPC243420 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	27367
0.1-0.2	20616
0.2-0.3	1624
0.3-0.4	152
0.4-0.5	30
0.5-0.6	20
0.6-0.7	30
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC147743
0.8514	High Similarity	NPC4809
0.8514	High Similarity	NPC73517
0.8261	Intermediate Similarity	NPC155564
0.8052	Intermediate Similarity	NPC86630
0.7778	Intermediate Similarity	NPC159526
0.7763	Intermediate Similarity	NPC471404
0.7568	Intermediate Similarity	NPC46283
0.7568	Intermediate Similarity	NPC469944
0.7568	Intermediate Similarity	NPC134911
0.7284	Intermediate Similarity	NPC106601
0.7284	Intermediate Similarity	NPC151474
0.7195	Intermediate Similarity	NPC212614
0.7195	Intermediate Similarity	NPC478337
0.7195	Intermediate Similarity	NPC478338
0.7195	Intermediate Similarity	NPC205613
0.7073	Intermediate Similarity	NPC478340
0.7051	Intermediate Similarity	NPC478616
0.7051	Intermediate Similarity	NPC478339
0.6974	Remote Similarity	NPC272552
0.6974	Remote Similarity	NPC226108
0.6974	Remote Similarity	NPC322899
0.6867	Remote Similarity	NPC78074
0.6842	Remote Similarity	NPC211561
0.6712	Remote Similarity	NPC58190
0.6712	Remote Similarity	NPC108811
0.6712	Remote Similarity	NPC170103
0.6712	Remote Similarity	NPC236202
0.6712	Remote Similarity	NPC262911
0.6712	Remote Similarity	NPC202742
0.6622	Remote Similarity	NPC246202
0.6622	Remote Similarity	NPC224161
0.6622	Remote Similarity	NPC46335
0.6622	Remote Similarity	NPC279406
0.6622	Remote Similarity	NPC486519
0.6591	Remote Similarity	NPC478617
0.6582	Remote Similarity	NPC44192
0.6486	Remote Similarity	NPC601999
0.6216	Remote Similarity	NPC96576
0.6076	Remote Similarity	NPC70409
0.6076	Remote Similarity	NPC204770
0.6076	Remote Similarity	NPC600551
0.6076	Remote Similarity	NPC601980
0.6076	Remote Similarity	NPC602065
0.6076	Remote Similarity	NPC611024
0.6049	Remote Similarity	NPC278548
0.6	Remote Similarity	NPC601997
0.6	Remote Similarity	NPC609211
0.6	Remote Similarity	NPC610665
0.5844	Remote Similarity	NPC277331
0.5844	Remote Similarity	NPC100482
0.5833	Remote Similarity	NPC306267
0.5823	Remote Similarity	NPC313116
0.5823	Remote Similarity	NPC603340
0.5802	Remote Similarity	NPC226809
0.5652	Remote Similarity	NPC484331
0.5542	Remote Similarity	NPC600630
0.5542	Remote Similarity	NPC607896
0.5542	Remote Similarity	NPC611369
0.5529	Remote Similarity	NPC20050
0.5393	Remote Similarity	NPC9309
0.5375	Remote Similarity	NPC294558
0.5375	Remote Similarity	NPC18185
0.5375	Remote Similarity	NPC263940
0.5368	Remote Similarity	NPC484330
0.5286	Remote Similarity	NPC207179
0.5286	Remote Similarity	NPC167571
0.5286	Remote Similarity	NPC278552
0.5263	Remote Similarity	NPC12326

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC243420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5780
0.1-0.2	3342
0.2-0.3	23
0.3-0.4	3
0.4-0.5	2
0.5-0.6	0
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
		NPD

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