NPASS Compound

Natural Product: NPC480470

Natural Product ID	NPC480470
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AUOAGQOZVIPWBY-VNAKZTKISA-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]

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 98103 0 0 0 0 0 0 0 0999 V2000 9.6015 0.4343 3.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8546 1.2171 2.0933 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9777 1.2554 1.0231 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7904 0.5264 1.0156 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9474 0.5788 -0.0410 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3104 1.3826 -1.1134 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4620 2.0981 -1.1236 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3210 2.0529 -0.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5126 2.7841 -0.0525 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6641 -0.1439 -0.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1807 -0.9035 0.8060 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9375 -1.6425 0.8031 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5224 -2.3544 1.7190 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1274 -1.5529 -0.3266 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9008 -2.2330 -0.4214 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0674 -3.3446 -1.4457 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6054 -2.9424 -2.8061 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3015 -2.2122 -2.8644 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4477 -1.0026 -3.7123 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8681 -1.1288 -4.8968 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1506 0.2700 -3.2856 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1713 -1.9840 -1.5999 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7759 -1.3440 -0.7827 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1033 -0.8862 0.3456 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1211 0.4593 0.3722 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8037 1.2027 1.3391 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5924 0.6775 2.7334 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8892 0.5590 3.0434 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1511 1.2984 4.3636 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7960 2.6567 4.2224 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6649 1.1731 2.1051 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5064 0.8079 0.7912 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4948 -0.1629 0.4743 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6942 0.1073 -0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7067 0.2365 -1.4900 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6744 0.1036 -2.1790 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8709 0.5204 -2.1840 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0279 0.6721 -1.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2371 0.9617 -2.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2707 1.0953 -3.4555 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1167 0.9456 -4.2045 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9300 0.6591 -3.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7714 0.5083 -4.2990 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1999 1.0909 -5.5904 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4668 0.0107 -6.4556 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4855 1.3860 -4.0965 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9753 0.5415 -0.1556 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8791 0.2667 0.5557 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0499 0.1554 2.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1821 0.6817 2.5773 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4635 0.5517 3.9109 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5637 -0.1377 4.7013 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4211 -0.6742 4.1531 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1651 -0.5221 2.7834 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5270 -1.3606 4.9463 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8850 -0.2479 6.0496 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1914 -0.5614 2.9469 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3503 2.5290 1.3279 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5684 -2.1777 -3.4831 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3845 -4.5089 -1.0260 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9120 -0.6213 3.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2679 0.7749 4.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5390 0.5272 3.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5348 -0.0930 1.8623 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6587 1.4502 -1.9853 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7434 2.7306 -1.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3323 2.4194 0.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0824 -0.0362 -1.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7773 -1.0127 1.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7466 -2.7842 0.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1310 -3.6494 -1.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4924 -3.8841 -3.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4719 -2.8536 -3.3818 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2243 1.0427 -3.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0979 -0.4808 -1.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1446 0.9257 -0.6098 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8387 1.2195 1.0188 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0321 1.3471 3.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1197 -0.4942 3.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 1.1886 4.6594 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5489 0.9014 5.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3992 3.1401 4.8495 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7913 1.7191 0.1560 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1358 1.0775 -1.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7862 0.0433 -5.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0987 0.3842 -7.2947 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0713 -0.7805 -5.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5393 -0.4970 -6.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5878 1.1060 -5.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8784 1.2194 1.9538 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3781 0.9802 4.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2535 -0.9899 2.4036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8823 -2.0513 4.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4774 -0.9774 6.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1603 -0.4688 3.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 2.9609 0.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7948 -2.5556 -4.3754 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4537 -5.1467 -1.7729 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 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 18 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 28 29 1 0 29 30 1 0 28 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 41 44 1 0 44 45 1 0 40 46 1 0 38 47 1 0 47 48 1 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 53 55 1 0 52 56 1 0 27 57 1 0 26 58 1 0 17 59 1 0 16 60 1 0 8 3 1 0 23 15 1 0 32 25 1 0 48 34 2 0 54 49 1 0 42 37 1 0 1 61 1 0 1 62 1 0 1 63 1 0 4 64 1 0 6 65 1 0 7 66 1 0 9 67 1 0 10 68 1 0 11 69 1 0 15 70 1 1 16 71 1 6 17 72 1 6 18 73 1 6 21 74 1 0 23 75 1 6 25 76 1 6 26 77 1 6 27 78 1 1 28 79 1 1 29 80 1 0 29 81 1 0 30 82 1 0 32 83 1 6 39 84 1 0 43 85 1 0 45 86 1 0 45 87 1 0 45 88 1 0 46 89 1 0 50 90 1 0 51 91 1 0 54 92 1 0 55 93 1 0 56 94 1 0 57 95 1 0 58 96 1 0 59 97 1 0 60 98 1 0 M END

Standard InCHIKey	AUOAGQOZVIPWBY-VNAKZTKISA-N
Standard InCHI	InChI=1S/C38H38O22/c1-53-19-9-13(3-6-16(19)41)4-8-22(44)57-34-29(50)28(49)33(36(51)52)59-38(34)60-35-27(48)24(45)21(12-39)56-37(35)58-32-26(47)23-20(11-18(43)31(54-2)25(23)46)55-30(32)14-5-7-15(40)17(42)10-14/h3-11,21,24,27-29,33-35,37-43,45-46,48-50H,12H2,1-2H3,(H,51,52)/b8-4+/t21-,24-,27+,28+,29+,33-,34-,35-,37-,38+/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)O[C@@H]1[C@H]([C@@H]([C@H](C(=O)O)O[C@H]1O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@@H]1Oc1c(=O)c2c(cc(c(c2O)OC)O)oc1c1ccc(c(c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	846.19	Volume:	770.94 ? Van der Waals volume.
Dense:	1.098	LogP:	-0.367 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.784 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.904 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	39.0
TPSA:	351.49 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.048	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.306	Fsp³:	0.342
MCE-18:	149.255 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.739	Fluc inhibitor:	0.516 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.851 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.274	Promiscuous compounds:	0.446

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.391	MDCK Permeability:	-5.424
Pgp-inhibitor:	0.0	Pgp-substrate:	0.058
PAMPA:	1.0 ? 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):	0.351
20% Bioavailability (F20%):	0.767	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.245
Plasma Protein Binding (PPB):	74.17%	Volume Distribution (VD):	-0.276
Fu:	20.468% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.054
BSEP inhibitor:	0.003

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:	1.0
HLM stability:	0.034 ? 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):

0.768

Half-life (T1/2):

4.738

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.341	Drug-induced Liver Injury (DILI):	0.825
AMES Toxicity:	0.736	Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.04	Skin Sensitization:	1.0
Carcinogencity:	0.013	Eye Corrosion:	0.0
Eye Irritation:	0.156	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.969
Hematotoxicity:	0.038	Drug-induced Nephrotoxicity:	0.554
Genotoxicity:	0.868	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.657	Hek293 Cytotoxicity:	0.222
BCF:	0.47 ? 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:	3.141 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.829 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.032 ? 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
NPO40039	Atriplex tatarica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181926]

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
MIC	4
MBC	4
Inhibition	3

Activity Type	# Activity
Organism	11

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
NPT3888	Organism	Micrococcus flavus	Micrococcus flavus	MIC	=	295500.0	nM	PMID[31181926]
NPT3888	Organism	Micrococcus flavus	Micrococcus flavus	MBC	=	472.8	uM	PMID[31181926]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	886500.0	nM	PMID[31181926]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MBC	=	1182.0	uM	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	295500.0	nM	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MBC	=	472.8	uM	PMID[31181926]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	591000.0	nM	PMID[31181926]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	1182.0	uM	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	43.0	%	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	26.2	%	PMID[31181926]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	1.8	%	PMID[31181926]

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 NPC480470 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	16181
0.1-0.2	30173
0.2-0.3	2846
0.3-0.4	479
0.4-0.5	151
0.5-0.6	24
0.6-0.7	3
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	Natural Product ID
0.7094	Intermediate Similarity	NPC480472
0.629	Remote Similarity	NPC21359
0.629	Remote Similarity	NPC460984
0.6116	Remote Similarity	NPC470713
0.5935	Remote Similarity	NPC470719
0.5935	Remote Similarity	NPC470717
0.5929	Remote Similarity	NPC480471
0.5929	Remote Similarity	NPC488076
0.5902	Remote Similarity	NPC295625
0.5887	Remote Similarity	NPC470720
0.5827	Remote Similarity	NPC25946
0.5826	Remote Similarity	NPC472991
0.5537	Remote Similarity	NPC470416
0.5537	Remote Similarity	NPC488075
0.5512	Remote Similarity	NPC488078
0.5484	Remote Similarity	NPC470718
0.5431	Remote Similarity	NPC472992
0.5323	Remote Similarity	NPC470712
0.5273	Remote Similarity	NPC42773
0.5273	Remote Similarity	NPC45522
0.5214	Remote Similarity	NPC470444
0.52	Remote Similarity	NPC164704
0.5143	Remote Similarity	NPC487501
0.5122	Remote Similarity	NPC483765
0.5079	Remote Similarity	NPC470715
0.5077	Remote Similarity	NPC162394
0.5042	Remote Similarity	NPC488073
0.5041	Remote Similarity	NPC218161

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3887
0.1-0.2	5217
0.2-0.3	41
0.3-0.4	5
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