NPASS Compound

Natural Product: NPC75388

Natural Product ID	NPC75388
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SVMNNRZZJAFEJM-VSGBNLITSA-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:0001392] Lignans, neolignans and related compounds

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 79 86 0 0 0 0 0 0 0 0999 V2000 3.0965 -3.9367 -1.5837 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3036 -3.6977 -0.1461 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7204 -4.8096 0.5479 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2633 -5.0087 0.1976 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5512 -3.6820 0.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8343 -3.7239 0.1179 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5371 -2.5506 0.0731 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9168 -1.3293 0.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4685 -1.2990 0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2049 -2.4774 0.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6815 -2.4325 0.1377 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2228 -1.7854 1.3978 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0758 -0.6082 1.0280 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4022 -0.7310 0.6594 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1228 0.3827 0.2872 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5208 1.6466 0.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2092 1.7415 0.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4870 0.6206 1.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4858 2.9633 0.6670 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1286 2.8657 0.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1115 3.3725 1.0467 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2088 3.2389 0.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4751 2.6102 -0.5710 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5673 2.1131 -1.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8875 2.2287 -0.9202 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8479 2.4315 -1.0620 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9137 2.3472 -0.0342 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6909 1.0559 -0.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0574 0.9843 -0.0775 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8447 2.2417 -0.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0449 3.3333 0.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7437 3.4745 -0.0305 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2307 4.7626 -0.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7601 -0.2337 -0.0617 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0458 -1.3941 -0.0209 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6539 -1.3245 0.0028 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9779 -0.1300 -0.0138 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -0.1222 0.0094 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9470 -2.5362 0.0472 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7211 -2.5985 -0.0052 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0988 -2.7740 -0.0294 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2237 2.7700 -0.0932 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5710 2.6418 -0.4689 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0145 -5.0206 -1.7512 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9063 -3.4707 -2.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1307 -3.4862 -1.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8778 -4.7627 1.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2574 -5.7284 0.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1468 -5.5542 -0.7550 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8173 -5.6200 1.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3744 -4.6681 0.1335 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9885 -0.3717 0.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9667 -1.7562 -0.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8371 -2.4597 2.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3697 -1.4312 2.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8220 -1.7350 0.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1460 0.2415 0.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4666 0.7471 1.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3373 3.8616 1.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0081 3.6357 1.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3772 1.6141 -2.2613 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6924 1.8481 -1.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8403 1.4654 -1.6466 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0942 3.1898 -1.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4041 2.3017 0.9783 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0871 2.4248 -1.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7912 2.1222 0.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0864 3.2026 1.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5991 4.3012 0.3096 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1283 5.4617 -0.3280 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6734 4.9533 -1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7231 5.1370 0.6796 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8572 -0.2101 -0.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2888 -3.7289 -0.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5713 -2.9458 0.9590 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6439 -1.9995 -0.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6770 2.0251 -1.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1366 2.1402 0.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0441 3.6343 -0.6531 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 29 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 40 41 1 0 16 42 1 0 42 43 1 0 11 2 1 0 18 13 1 0 25 20 1 0 32 27 1 0 10 5 1 0 37 28 2 0 39 7 1 0 38 8 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 6 51 1 0 9 52 1 0 11 53 1 6 12 54 1 0 12 55 1 0 14 56 1 0 15 57 1 0 18 58 1 0 21 59 1 0 22 60 1 0 24 61 1 0 25 62 1 0 26 63 1 0 26 64 1 0 27 65 1 1 30 66 1 0 30 67 1 0 31 68 1 0 31 69 1 0 33 70 1 0 33 71 1 0 33 72 1 0 34 73 1 0 41 74 1 0 41 75 1 0 41 76 1 0 43 77 1 0 43 78 1 0 43 79 1 0 M END

Standard InCHIKey	SVMNNRZZJAFEJM-VSGBNLITSA-N
Standard InCHI	InChI=1S/C36H36N2O5/c1-37-13-11-23-18-31-32-20-26(23)27(37)16-22-7-10-29(39-3)30(17-22)41-25-8-5-21(6-9-25)15-28-34-24(12-14-38(28)2)19-33(40-4)35(42-31)36(34)43-32/h5-10,17-20,27-28H,11-16H2,1-4H3/t27-,28-/m1/s1
SMILES	CN1CCc2cc3c4cc2[C@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@@H]1c2c(CCN1C)cc(c(c2O4)O3)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.26	Volume:	597.067 ? Van der Waals volume.
Dense:	0.965	LogP:	3.859 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.778 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	44.0
TPSA:	52.63 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	9.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.219	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.872	Fsp³:	0.333
MCE-18:	140.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.035 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.846 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.982 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.29

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.634	MDCK Permeability:	-4.799
Pgp-inhibitor:	0.592	Pgp-substrate:	0.91
PAMPA:	0.004 ? 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%):	0.643	30% Bioavailability (F30%):	0.875
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974	MRP1:	0.973
Plasma Protein Binding (PPB):	79.297%	Volume Distribution (VD):	0.33
Fu:	20.769% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.672
OATP1B3 inhibitor:	0.756	BCRP inhibitor:	0.783
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.997	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.877	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.043
CYP2B6-substrate:	0.417	CYP2C8-inhibitor:	0.025
HLM stability:	0.042 ? 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):

9.158

Half-life (T1/2):

2.918

ADMET: Toxicity

hERG Blockers:	0.911	hERG Blockers (10um):	0.85
Human Hepatotoxicity (H-HT):	0.665	Drug-induced Liver Injury (DILI):	0.03
AMES Toxicity:	0.752	Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	0.585
Carcinogencity:	0.876	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.917
Drug-induced Neurotoxicity:	0.91	Ototoxicity:	0.384
Hematotoxicity:	0.097	Drug-induced Nephrotoxicity:	0.433
Genotoxicity:	0.888	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.277	Hek293 Cytotoxicity:	0.659
BCF:	2.134 ? 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:	4.801 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.143 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.715 ? 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
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1516	Passiflora suberosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5156	Hypoestes rosea	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7389	Rhodiola atuntsuensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6730	Crossopteryx febrifuga	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1516	Passiflora suberosa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19931	Pyrus x nivalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24372	Artemisia palustris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23450	Chionographis japonica	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	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 NPC75388 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	34776
0.1-0.2	14470
0.2-0.3	368
0.3-0.4	110
0.4-0.5	34
0.5-0.6	38
0.6-0.7	30
0.7-0.8	2
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12424
1.0	High Similarity	NPC129518
1.0	High Similarity	NPC251580
0.8358	Intermediate Similarity	NPC76682
0.8358	Intermediate Similarity	NPC10908
0.8358	Intermediate Similarity	NPC63646
0.8358	Intermediate Similarity	NPC317145
0.8358	Intermediate Similarity	NPC198498
0.8358	Intermediate Similarity	NPC115284
0.8235	Intermediate Similarity	NPC276890
0.7971	Intermediate Similarity	NPC41376
0.7838	Intermediate Similarity	NPC274716
0.7838	Intermediate Similarity	NPC167116
0.7838	Intermediate Similarity	NPC609821
0.7778	Intermediate Similarity	NPC73492
0.7778	Intermediate Similarity	NPC299990
0.7538	Intermediate Similarity	NPC247639
0.7538	Intermediate Similarity	NPC25084
0.7467	Intermediate Similarity	NPC254441
0.7397	Intermediate Similarity	NPC603853
0.7333	Intermediate Similarity	NPC311973
0.7297	Intermediate Similarity	NPC290582
0.7297	Intermediate Similarity	NPC217748
0.7297	Intermediate Similarity	NPC182052
0.7297	Intermediate Similarity	NPC271013
0.7297	Intermediate Similarity	NPC42663
0.7297	Intermediate Similarity	NPC15414
0.7297	Intermediate Similarity	NPC480587
0.7215	Intermediate Similarity	NPC249996
0.72	Intermediate Similarity	NPC279228
0.7123	Intermediate Similarity	NPC227060
0.7037	Intermediate Similarity	NPC239584
0.7013	Intermediate Similarity	NPC116465
0.6883	Remote Similarity	NPC239824
0.6795	Remote Similarity	NPC185639
0.6795	Remote Similarity	NPC251735
0.6795	Remote Similarity	NPC49075
0.6795	Remote Similarity	NPC599951
0.6667	Remote Similarity	NPC139783
0.6667	Remote Similarity	NPC65312
0.6667	Remote Similarity	NPC611798
0.6582	Remote Similarity	NPC223690
0.6582	Remote Similarity	NPC9532
0.6567	Remote Similarity	NPC317439
0.6447	Remote Similarity	NPC603603
0.6386	Remote Similarity	NPC24260
0.6296	Remote Similarity	NPC229373
0.6279	Remote Similarity	NPC254581
0.622	Remote Similarity	NPC181796
0.622	Remote Similarity	NPC290005
0.622	Remote Similarity	NPC54654
0.622	Remote Similarity	NPC7715
0.622	Remote Similarity	NPC328155
0.622	Remote Similarity	NPC222661
0.622	Remote Similarity	NPC285931
0.619	Remote Similarity	NPC485712
0.6163	Remote Similarity	NPC480590
0.6145	Remote Similarity	NPC195538
0.6071	Remote Similarity	NPC212237
0.6071	Remote Similarity	NPC475479
0.6071	Remote Similarity	NPC243454
0.6071	Remote Similarity	NPC323537
0.6	Remote Similarity	NPC611658
0.5926	Remote Similarity	NPC608819
0.5889	Remote Similarity	NPC85381
0.5854	Remote Similarity	NPC475393
0.5843	Remote Similarity	NPC485711
0.5824	Remote Similarity	NPC191132
0.5795	Remote Similarity	NPC480586
0.5789	Remote Similarity	NPC30779
0.5765	Remote Similarity	NPC16357
0.5765	Remote Similarity	NPC302245
0.573	Remote Similarity	NPC281581
0.5682	Remote Similarity	NPC10871
0.5672	Remote Similarity	NPC213206
0.5672	Remote Similarity	NPC188163
0.5672	Remote Similarity	NPC328750
0.5663	Remote Similarity	NPC286119
0.5658	Remote Similarity	NPC317272
0.5658	Remote Similarity	NPC268503
0.5652	Remote Similarity	NPC60295
0.5616	Remote Similarity	NPC104196
0.5522	Remote Similarity	NPC314682
0.5443	Remote Similarity	NPC256012
0.5443	Remote Similarity	NPC610965
0.5385	Remote Similarity	NPC11296
0.5385	Remote Similarity	NPC274661
0.5385	Remote Similarity	NPC82457
0.5294	Remote Similarity	NPC112248
0.5281	Remote Similarity	NPC8836
0.5281	Remote Similarity	NPC275680
0.5281	Remote Similarity	NPC22115
0.5217	Remote Similarity	NPC206900
0.5213	Remote Similarity	NPC475597
0.5213	Remote Similarity	NPC41122
0.5213	Remote Similarity	NPC318805
0.5204	Remote Similarity	NPC256124
0.5185	Remote Similarity	NPC480592
0.5181	Remote Similarity	NPC240841
0.5119	Remote Similarity	NPC480591
0.5056	Remote Similarity	NPC302275

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC75388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5192
0.1-0.2	3859
0.2-0.3	85
0.3-0.4	8
0.4-0.5	2
0.5-0.6	1
0.6-0.7	0
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8358	Intermediate Similarity	NPD8099	Discontinued
0.7887	Intermediate Similarity	NPD8156	Discontinued
0.7297	Intermediate Similarity	NPD8095	Phase 1
0.5672	Remote Similarity	NPD4664	Clinical (unspecified phase)

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