NPASS Compound

Natural Product: NPC479448

Natural Product ID	NPC479448
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SOZKSILYEYHONB-GSILGGMYSA-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:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 94 98 0 0 0 0 0 0 0 0999 V2000 -2.6655 4.3367 0.4257 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6860 3.3541 0.7425 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9586 2.0133 0.8695 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2282 1.4565 0.7097 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4501 0.1125 0.8484 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8181 -0.3946 0.6496 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1692 -1.6483 0.7663 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5049 -2.1943 0.5758 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4983 -1.3677 0.2349 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4170 -0.7485 -0.9810 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4122 -1.4639 -1.9685 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8043 -1.3891 -1.4360 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9177 -0.2392 -0.4771 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0544 0.9004 -0.9434 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2456 2.0374 0.0693 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6004 2.3624 0.1537 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7038 0.5973 -1.0061 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2428 0.2060 -0.5319 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1403 -2.5774 -0.7810 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2289 -0.8276 -3.1768 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3874 -0.6961 1.1534 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1049 -0.1461 1.3167 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2096 -0.7918 1.6534 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0513 -1.5535 2.9581 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1123 -2.1911 3.3571 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1575 0.3438 1.8338 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4350 0.1812 1.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9256 -1.0242 0.6827 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1143 -1.1251 -0.0606 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8144 -0.0111 -0.4319 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3022 1.2302 -0.0447 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1350 1.3203 0.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9567 2.4011 -0.3846 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4147 3.6371 0.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9545 -0.0643 -1.1399 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2945 -0.0317 -0.6923 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0930 -1.2589 -0.9888 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3717 -1.1115 -0.1411 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0636 0.1634 -0.4655 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2448 1.2361 -1.0761 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8413 1.4687 -2.4875 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2072 1.6683 -2.3734 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9264 1.0537 -1.2521 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5632 0.6797 0.7571 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2262 -2.1766 -0.3630 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5120 -2.4579 -0.6766 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5214 -2.3855 -0.3868 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7949 -3.5207 -0.0051 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4691 1.4832 1.3844 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8614 1.1845 1.1827 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3278 5.3524 0.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5721 4.0890 1.0196 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8941 4.2843 -0.6601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0587 2.1316 0.4676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6156 0.3024 0.4037 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3263 -2.3227 1.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4085 -2.9564 -0.2752 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8452 -2.7733 1.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4502 -0.9398 -1.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0790 -2.5045 -1.9960 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5533 -1.2663 -2.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6751 -0.5664 0.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4716 1.2771 -1.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7228 2.9585 -0.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9204 1.6903 1.0730 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7569 2.8485 0.9988 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7861 -0.2050 0.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5765 -2.3959 0.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7999 -1.2192 -3.8775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4957 -1.7553 1.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4873 -1.4854 0.8441 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -2.2915 2.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 -0.8341 3.7186 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0341 -3.1479 3.1210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4490 0.4948 2.9100 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4017 -1.9275 0.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7202 2.2844 0.9935 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1945 4.4379 -0.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2016 3.6530 1.1327 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4610 3.8928 -0.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2270 0.0327 0.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4222 -1.2105 -2.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0283 -1.1502 0.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9825 -0.0697 -1.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4130 2.2431 -0.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7044 0.5129 -3.0732 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3059 2.2447 -3.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7077 1.2333 -3.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7031 -0.0159 1.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6697 -2.4027 0.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2146 -3.0761 -0.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7266 -3.6161 1.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2693 -4.4560 -0.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7452 -3.4061 -0.3883 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 1 0 6 7 2 0 7 8 1 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 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 30 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 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 29 47 1 0 47 48 1 0 26 49 1 0 49 50 1 0 50 3 1 0 17 10 1 0 50 22 2 0 32 27 1 0 43 36 1 0 1 51 1 0 1 52 1 0 1 53 1 0 4 54 1 0 6 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 10 59 1 6 11 60 1 6 12 61 1 6 13 62 1 1 14 63 1 6 15 64 1 0 15 65 1 0 16 66 1 0 18 67 1 0 19 68 1 0 20 69 1 0 21 70 1 0 23 71 1 6 24 72 1 0 24 73 1 0 25 74 1 0 26 75 1 1 28 76 1 0 32 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 36 81 1 1 37 82 1 6 38 83 1 1 39 84 1 6 40 85 1 1 41 86 1 0 41 87 1 0 42 88 1 0 44 89 1 0 45 90 1 0 46 91 1 0 48 92 1 0 48 93 1 0 48 94 1 0 M END

Standard InCHIKey	SOZKSILYEYHONB-GSILGGMYSA-N
Standard InCHI	InChI=1S/C33H44O17/c1-43-18-8-14(5-4-6-46-32-27(41)25(39)23(37)21(12-35)47-32)7-16-17(11-34)29(49-30(16)18)15-9-19(44-2)31(20(10-15)45-3)50-33-28(42)26(40)24(38)22(13-36)48-33/h4-5,7-10,17,21-29,32-42H,6,11-13H2,1-3H3/b5-4+/t17-,21+,22+,23+,24+,25-,26-,27+,28+,29+,32+,33-/m0/s1
SMILES	COc1cc(/C=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)cc2[C@H](CO)[C@@H](c3cc(c(c(c3)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)OC)Oc12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	712.26	Volume:	667.52 ? Van der Waals volume.
Dense:	1.067	LogP:	0.387 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.048 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.625 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	29.0
TPSA:	255.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.108	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.129	Fsp³:	0.576
MCE-18:	121.154 ? 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:	0.482	Fluc inhibitor:	0.257 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.074 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.437 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.119	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.804	MDCK Permeability:	-5.237
Pgp-inhibitor:	0.0	Pgp-substrate:	0.186
PAMPA:	0.927 ? 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):	0.692
20% Bioavailability (F20%):	0.05	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021	MRP1:	0.003
Plasma Protein Binding (PPB):	73.405%	Volume Distribution (VD):	-0.256
Fu:	23.731% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.292
BSEP inhibitor:	0.012

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.064
HLM stability:	0.012 ? 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):

1.331

Half-life (T1/2):

3.975

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.857	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.976	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.011	Skin Sensitization:	1.0
Carcinogencity:	0.094	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.999
Hematotoxicity:	0.683	Drug-induced Nephrotoxicity:	0.936
Genotoxicity:	0.431	RPMI-8226 Immunitoxicity:	0.272
A549 Cytotoxicity:	0.796	Hek293 Cytotoxicity:	0.428
BCF:	0.765 ? 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:	3.351 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.313 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.2 ? 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
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18991207]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	essential oil	Tibet	n.a.	PMID[20944522]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28541690]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36552598]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37746728]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39013008]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39395223]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29110	Litsea cubeba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29110	Litsea cubeba	Species	Lauraceae	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
Activity	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
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	30.5	%	PMID[28541690]

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 NPC479448 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	22171
0.1-0.2	24083
0.2-0.3	2798
0.3-0.4	706
0.4-0.5	75
0.5-0.6	11
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9014	High Similarity	NPC270751
0.8333	Intermediate Similarity	NPC269559
0.7195	Intermediate Similarity	NPC302610
0.7183	Intermediate Similarity	NPC470236
0.6707	Remote Similarity	NPC43508
0.6667	Remote Similarity	NPC173726
0.6625	Remote Similarity	NPC199539
0.6506	Remote Similarity	NPC478701
0.625	Remote Similarity	NPC162093
0.5657	Remote Similarity	NPC228357
0.5556	Remote Similarity	NPC241600
0.5467	Remote Similarity	NPC49074
0.5455	Remote Similarity	NPC217635
0.5325	Remote Similarity	NPC210478
0.5269	Remote Similarity	NPC224674
0.5269	Remote Similarity	NPC64475
0.5128	Remote Similarity	NPC132895
0.5125	Remote Similarity	NPC302378
0.5125	Remote Similarity	NPC232673
0.5062	Remote Similarity	NPC307110

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5475
0.1-0.2	3601
0.2-0.3	67
0.3-0.4	7
0.4-0.5	0
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