NPASS Compound

Natural Product: NPC307007

Natural Product ID	NPC307007
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PBLWZMSRSJTRHJ-NCIRKIHRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10009802
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 92 96 0 0 0 0 0 0 0 0999 V2000 4.6570 2.4572 -2.9503 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2918 1.8381 -1.8527 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7967 0.6839 -1.2766 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6486 0.1271 -1.7947 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0799 -1.0372 -1.2743 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7083 -1.6143 -0.2201 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8623 -1.0802 0.3235 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4273 0.0924 -0.2069 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5552 0.5488 0.3822 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3712 1.6309 0.1742 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4623 2.3777 1.5223 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7308 1.2640 2.5359 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9461 0.4756 2.1844 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2185 0.3139 0.7291 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9404 -1.1186 0.2471 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5371 -2.0098 1.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6858 1.2551 -0.1026 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0620 0.9672 2.8678 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5722 0.4939 2.5956 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4520 3.3336 1.5070 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9155 -1.5733 -1.9334 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6014 -0.9166 -1.7566 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3700 -1.7444 -2.6533 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7866 -2.7145 -1.7893 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1012 -2.0556 -0.5936 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5078 -1.7190 -0.5547 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3892 -2.6579 -1.1058 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7402 -2.4563 -1.1241 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3338 -1.2880 -0.5883 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4502 -0.3787 -0.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0606 -0.5892 -0.0340 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8955 0.7869 0.4968 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0068 1.7190 1.0468 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6834 -1.1612 -0.6460 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4932 -0.1688 -0.2193 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3524 0.4402 -1.3382 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0361 1.6433 -0.7108 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9060 1.1146 0.4155 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0167 0.3042 1.3330 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7450 -0.2221 2.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8470 -0.9137 3.3270 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4734 -0.7732 0.6338 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4569 2.1482 1.1624 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8148 2.3112 -1.6489 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5761 0.9010 -2.3770 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1171 -0.9231 -0.4789 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7276 -1.0858 0.7640 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1519 -1.0376 1.8907 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6213 1.7546 -3.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1978 3.3793 -3.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6198 2.7023 -2.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1760 0.6314 -2.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3378 -2.5438 0.2418 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3196 -1.5754 1.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0913 2.3430 -0.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4532 2.7789 1.7856 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8593 1.7244 3.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7927 -0.5647 2.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3440 0.4021 0.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4455 -1.3032 -0.7182 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8756 -1.3708 0.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5120 -2.0446 0.9260 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7128 1.3191 2.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7448 -0.4390 2.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1103 4.1654 1.9627 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7501 -2.6751 -1.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1858 -1.6655 -3.0385 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6254 0.1364 -2.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1619 -2.1527 -3.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2499 -1.1143 -2.9184 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8748 -2.7771 0.2169 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0081 -3.5917 -1.5419 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4448 -3.1713 -1.5455 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4056 0.1404 0.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2685 1.9865 0.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6068 2.5923 1.3666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5096 1.2064 1.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0352 0.6750 0.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1464 -0.2610 -1.6494 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2937 2.3143 -0.2266 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7158 0.4768 0.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1587 0.9525 1.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1327 0.6556 3.0936 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5607 -0.8790 2.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9232 -0.6036 3.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4129 3.0251 0.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5270 2.0189 -2.5356 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0516 0.1885 -2.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6449 0.0724 -0.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4519 -0.2834 0.8776 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1675 -2.0943 0.8237 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5234 -1.9385 2.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 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 1 0 14 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 5 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 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 25 46 1 0 46 47 1 0 47 48 1 0 8 3 1 0 17 10 1 0 46 22 1 0 31 26 1 0 42 35 1 0 1 49 1 0 1 50 1 0 1 51 1 0 4 52 1 0 6 53 1 0 7 54 1 0 10 55 1 6 11 56 1 1 12 57 1 1 13 58 1 1 14 59 1 1 15 60 1 0 15 61 1 0 16 62 1 0 18 63 1 0 19 64 1 0 20 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 23 69 1 0 23 70 1 0 25 71 1 1 27 72 1 0 28 73 1 0 31 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 35 78 1 1 36 79 1 6 37 80 1 1 38 81 1 6 39 82 1 1 40 83 1 0 40 84 1 0 41 85 1 0 43 86 1 0 44 87 1 0 45 88 1 0 46 89 1 1 47 90 1 0 47 91 1 0 48 92 1 0 M END

Standard InCHIKey	PBLWZMSRSJTRHJ-NCIRKIHRSA-N
Standard InCHI	InChI=1S/C32H44O16/c1-42-20-8-14(3-5-18(20)45-31-28(40)26(38)24(36)22(11-34)47-31)7-16-13-44-30(17(16)10-33)15-4-6-19(21(9-15)43-2)46-32-29(41)27(39)25(37)23(12-35)48-32/h3-6,8-9,16-17,22-41H,7,10-13H2,1-2H3/t16-,17-,22+,23+,24+,25+,26-,27-,28+,29+,30+,31+,32+/m0/s1
SMILES	COc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C[C@H]1CO[C@H](c2ccc(c(c2)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@H]1CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	684.26	Volume:	644.071 ? Van der Waals volume.
Dense:	1.062	LogP:	-0.537 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.279 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.089 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	29.0
TPSA:	246.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.985	Fsp³:	0.625
MCE-18:	120.308 ? 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:	0.491	Fluc inhibitor:	0.047 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.042 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.047 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.094	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.539	MDCK Permeability:	-5.227
Pgp-inhibitor:	0.0	Pgp-substrate:	0.589
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):	0.79
20% Bioavailability (F20%):	0.041	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.006
Plasma Protein Binding (PPB):	69.835%	Volume Distribution (VD):	-0.35
Fu:	27.779% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.014
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.001
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):

1.239

Half-life (T1/2):

4.988

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.012
Human Hepatotoxicity (H-HT):	0.968	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.992	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.104	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.999
Hematotoxicity:	0.635	Drug-induced Nephrotoxicity:	0.973
Genotoxicity:	0.902	RPMI-8226 Immunitoxicity:	0.191
A549 Cytotoxicity:	0.347	Hek293 Cytotoxicity:	0.163
BCF:	0.692 ? 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:	3.274 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.744 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.907 ? 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
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32004936]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39053741]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4554	Isatis tinctoria	Species	Brassicaceae	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 NPC307007 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	14700
0.1-0.2	31027
0.2-0.3	3299
0.3-0.4	650
0.4-0.5	117
0.5-0.6	41
0.6-0.7	12
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471063
0.8472	Intermediate Similarity	NPC185307
0.8472	Intermediate Similarity	NPC470950
0.8451	Intermediate Similarity	NPC39657
0.7313	Intermediate Similarity	NPC276753
0.7313	Intermediate Similarity	NPC205796
0.7206	Intermediate Similarity	NPC246947
0.6875	Remote Similarity	NPC206882
0.6842	Remote Similarity	NPC605526
0.6622	Remote Similarity	NPC158635
0.6622	Remote Similarity	NPC229882
0.6533	Remote Similarity	NPC286235
0.6447	Remote Similarity	NPC38041
0.6447	Remote Similarity	NPC22150
0.6447	Remote Similarity	NPC279298
0.6176	Remote Similarity	NPC472024
0.6176	Remote Similarity	NPC270849
0.6087	Remote Similarity	NPC26653
0.6087	Remote Similarity	NPC80600
0.5976	Remote Similarity	NPC299706
0.5976	Remote Similarity	NPC245615
0.5976	Remote Similarity	NPC186316
0.5976	Remote Similarity	NPC115466
0.5976	Remote Similarity	NPC61604
0.5952	Remote Similarity	NPC129417
0.5952	Remote Similarity	NPC470235
0.5952	Remote Similarity	NPC283995
0.589	Remote Similarity	NPC64201
0.5857	Remote Similarity	NPC47181
0.5833	Remote Similarity	NPC478055
0.5694	Remote Similarity	NPC95392
0.5694	Remote Similarity	NPC84013
0.5694	Remote Similarity	NPC55715
0.5694	Remote Similarity	NPC35877
0.5652	Remote Similarity	NPC9912
0.5647	Remote Similarity	NPC163635
0.5581	Remote Similarity	NPC112861
0.5507	Remote Similarity	NPC166040
0.5432	Remote Similarity	NPC18979
0.5412	Remote Similarity	NPC486098
0.5405	Remote Similarity	NPC302378
0.5402	Remote Similarity	NPC486548
0.5402	Remote Similarity	NPC476356
0.5395	Remote Similarity	NPC37468
0.5357	Remote Similarity	NPC217635
0.5342	Remote Similarity	NPC248355
0.5316	Remote Similarity	NPC486102
0.5309	Remote Similarity	NPC51328
0.5309	Remote Similarity	NPC55158
0.53	Remote Similarity	NPC475224
0.5287	Remote Similarity	NPC46092
0.527	Remote Similarity	NPC55040
0.5195	Remote Similarity	NPC486107
0.519	Remote Similarity	NPC216129
0.519	Remote Similarity	NPC130449
0.519	Remote Similarity	NPC248132
0.5125	Remote Similarity	NPC486104
0.5111	Remote Similarity	NPC486097
0.506	Remote Similarity	NPC227902
0.5056	Remote Similarity	NPC486549

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC307007 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3736
0.1-0.2	5237
0.2-0.3	167
0.3-0.4	9
0.4-0.5	1
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