NPASS Compound

Natural Product: NPC50759

Natural Product ID	NPC50759
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PEFASEPMJYRQBW-MTYWJFCJSA-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:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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 97 0 0 0 0 0 0 0 0999 V2000 -5.6201 4.7058 -0.6293 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5821 3.6982 0.4706 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5692 4.0701 1.5601 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5119 3.0661 2.6936 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4500 1.6572 2.1994 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4734 1.5516 1.0752 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3369 0.2559 0.5923 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9634 -0.0596 0.6433 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7246 -1.4641 0.1424 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2022 -1.6607 -1.2954 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2802 -3.1787 -1.4432 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2420 -3.8833 -0.5803 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0722 -3.0700 -0.2621 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4038 -1.7670 0.1881 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1364 -2.9241 -1.3598 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1719 -2.5269 -1.1702 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3580 -1.1098 -1.0273 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6243 -0.3719 -1.0863 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6099 -0.6058 -0.8327 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8400 0.7406 -0.6852 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0820 1.2867 -0.4816 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1439 0.4162 -0.4265 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9454 -0.9649 -0.5745 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6695 -1.4630 -0.7769 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4608 -2.7439 -0.9125 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2662 -3.3060 -1.1056 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2390 -4.7751 -1.2433 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1405 -5.5354 -1.4331 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2405 -6.9037 -1.5556 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4678 -7.5596 -1.4930 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5749 -6.7859 -1.3034 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4850 -5.4310 -1.1790 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5147 -8.9426 -1.6223 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4185 0.8621 -0.2248 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8560 2.1806 -0.0078 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6381 2.6002 -1.2128 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6944 3.6432 -0.9629 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4229 3.2655 0.3290 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4080 3.1795 1.4323 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1856 2.7822 2.6961 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5206 2.1820 1.1887 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3993 4.1853 0.6246 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6400 3.4978 -2.0087 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7077 3.1399 -2.1406 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7191 1.5857 -0.7518 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8668 -4.4058 0.5810 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2007 -3.5544 -2.7798 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4065 -1.0354 -1.5188 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9152 2.4043 0.0293 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0050 0.8785 3.2924 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5708 3.3201 3.5498 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2067 5.3103 2.0616 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5937 4.7838 -1.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8759 5.6959 -0.1806 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3227 4.3748 -1.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5695 3.6516 0.9517 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5705 4.1473 1.1132 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5752 3.2494 3.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4577 1.2626 1.9388 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5028 1.9713 1.3975 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3764 0.6910 0.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6678 -0.0455 1.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2614 -2.1606 0.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4016 -1.3518 -1.9970 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2718 -3.5197 -1.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9783 -4.7849 -1.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4832 -3.4692 0.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1613 2.3682 -0.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7606 -1.6442 -0.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8033 -5.1040 -1.5128 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6505 -7.5020 -1.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5652 -7.2246 -1.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 -4.8720 -1.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9527 -9.5475 -1.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9606 2.8654 0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1343 1.7072 -1.6561 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3125 4.6694 -0.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8338 2.2469 0.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8790 4.1454 1.5896 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6950 1.8260 2.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9234 3.5780 2.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4774 2.5739 3.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6400 4.7712 -0.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6898 4.3496 -2.5392 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1846 3.7934 -2.7141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8710 2.4973 -1.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2267 -4.4576 1.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9198 -4.5033 -2.8037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3313 -0.5208 -2.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7018 0.2764 3.6314 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4078 2.8637 3.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9407 5.9111 2.2564 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 1 0 6 7 1 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 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 30 33 1 0 22 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 39 41 1 0 38 42 1 0 37 43 1 0 36 44 1 0 20 45 1 0 12 46 1 0 11 47 1 0 10 48 1 0 6 49 1 0 5 50 1 0 4 51 1 0 3 52 1 0 49 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 41 35 1 0 24 19 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 1 3 57 1 6 4 58 1 1 5 59 1 6 6 60 1 1 8 61 1 0 8 62 1 0 9 63 1 1 10 64 1 6 11 65 1 1 12 66 1 6 13 67 1 1 21 68 1 0 23 69 1 0 28 70 1 0 29 71 1 0 31 72 1 0 32 73 1 0 33 74 1 0 35 75 1 1 36 76 1 6 37 77 1 1 38 78 1 6 39 79 1 1 40 80 1 0 40 81 1 0 40 82 1 0 42 83 1 0 43 84 1 0 44 85 1 0 45 86 1 0 46 87 1 0 47 88 1 0 48 89 1 0 50 90 1 0 51 91 1 0 52 92 1 0 M END

Standard InCHIKey	PEFASEPMJYRQBW-MTYWJFCJSA-N
Standard InCHI	InChI=1S/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3/t10-,11-,17-,19-,20-,21-,23+,24+,25+,26-,27-,28-,31-,32+,33+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](OC[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(cc2)O)O[C@@H]2[C@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.22	Volume:	673.908 ? Van der Waals volume.
Dense:	1.098	LogP:	0.67 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.21 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.418 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	36.0
TPSA:	308.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

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:	5.291	Fsp³:	0.545
MCE-18:	150.706 ? 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:	0.66	Fluc inhibitor:	0.299 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.697 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.502 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.161	Promiscuous compounds:	0.524

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.654	MDCK Permeability:	-4.949
Pgp-inhibitor:	0.0	Pgp-substrate:	0.913
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):	0.68
20% Bioavailability (F20%):	0.017	30% Bioavailability (F30%):	0.982
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.005
Plasma Protein Binding (PPB):	78.973%	Volume Distribution (VD):	-0.088
Fu:	19.467% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.374
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:	0.352
HLM stability:	0.04 ? 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):

0.913

Half-life (T1/2):

6.401

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.093
Human Hepatotoxicity (H-HT):	0.47	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.942	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.007	Skin Sensitization:	0.996
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.012	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.993
Hematotoxicity:	0.037	Drug-induced Nephrotoxicity:	0.732
Genotoxicity:	0.712	RPMI-8226 Immunitoxicity:	0.273
A549 Cytotoxicity:	0.591	Hek293 Cytotoxicity:	0.512
BCF:	0.452 ? 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:	3.06 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.605 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.671 ? 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
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38005295]
NPO6418	Passalora rosicola	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19510	Origanum floribundum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23040	Methylomonas methanica	Species	Methylococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14708	Macowania corymbosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13937	Leptodontidium elatius	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19165	Comptonia peregrina	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16769	Baccharis hutchisonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16769	Baccharis hutchisonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14708	Macowania corymbosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19510	Origanum floribundum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19165	Comptonia peregrina	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23040	Methylomonas methanica	Species	Methylococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6418	Passalora rosicola	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13937	Leptodontidium elatius	Species	n.a.	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 NPC50759 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	21255
0.1-0.2	24949
0.2-0.3	2723
0.3-0.4	419
0.4-0.5	253
0.5-0.6	102
0.6-0.7	62
0.7-0.8	2
0.8-0.85	9
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	NPC186816
0.8312	Intermediate Similarity	NPC249281
0.8101	Intermediate Similarity	NPC46420
0.8095	Intermediate Similarity	NPC173582
0.8095	Intermediate Similarity	NPC265885
0.8095	Intermediate Similarity	NPC181465
0.8095	Intermediate Similarity	NPC215710
0.8095	Intermediate Similarity	NPC473438
0.8095	Intermediate Similarity	NPC253788
0.8049	Intermediate Similarity	NPC276377
0.7882	Intermediate Similarity	NPC44931
0.7849	Intermediate Similarity	NPC25523
0.7753	Intermediate Similarity	NPC142142
0.7711	Intermediate Similarity	NPC116458
0.7711	Intermediate Similarity	NPC246943
0.7586	Intermediate Similarity	NPC65563
0.7586	Intermediate Similarity	NPC470949
0.7586	Intermediate Similarity	NPC150164
0.75	Intermediate Similarity	NPC473571
0.75	Intermediate Similarity	NPC110941
0.7471	Intermediate Similarity	NPC67105
0.7386	Intermediate Similarity	NPC203259
0.7386	Intermediate Similarity	NPC33054
0.7386	Intermediate Similarity	NPC210073
0.7386	Intermediate Similarity	NPC176740
0.7386	Intermediate Similarity	NPC471725
0.7386	Intermediate Similarity	NPC134532
0.7386	Intermediate Similarity	NPC602582
0.7253	Intermediate Similarity	NPC32641
0.7253	Intermediate Similarity	NPC256188
0.7253	Intermediate Similarity	NPC72016
0.7229	Intermediate Similarity	NPC271692
0.7143	Intermediate Similarity	NPC470443
0.7113	Intermediate Similarity	NPC480441
0.7108	Intermediate Similarity	NPC297987
0.7065	Intermediate Similarity	NPC35119
0.6966	Remote Similarity	NPC471079
0.6915	Remote Similarity	NPC476472
0.6915	Remote Similarity	NPC294815
0.6915	Remote Similarity	NPC473073
0.6915	Remote Similarity	NPC16194
0.6897	Remote Similarity	NPC605784
0.6889	Remote Similarity	NPC39834
0.6889	Remote Similarity	NPC227508
0.6848	Remote Similarity	NPC126784
0.6848	Remote Similarity	NPC241423
0.6813	Remote Similarity	NPC22062
0.6813	Remote Similarity	NPC473634
0.6813	Remote Similarity	NPC303913
0.6813	Remote Similarity	NPC138811
0.6804	Remote Similarity	NPC121703
0.6706	Remote Similarity	NPC158674
0.6702	Remote Similarity	NPC209296
0.6702	Remote Similarity	NPC473327
0.6667	Remote Similarity	NPC111929
0.6667	Remote Similarity	NPC320283
0.6667	Remote Similarity	NPC240306
0.6667	Remote Similarity	NPC41121
0.6667	Remote Similarity	NPC611303
0.6596	Remote Similarity	NPC12013
0.6596	Remote Similarity	NPC11432
0.6596	Remote Similarity	NPC477613
0.6588	Remote Similarity	NPC108831
0.6588	Remote Similarity	NPC182634
0.6566	Remote Similarity	NPC189564
0.6495	Remote Similarity	NPC101636
0.6471	Remote Similarity	NPC331652
0.6465	Remote Similarity	NPC203145
0.6452	Remote Similarity	NPC156869
0.6364	Remote Similarity	NPC14187
0.6344	Remote Similarity	NPC67326
0.6327	Remote Similarity	NPC221342
0.6327	Remote Similarity	NPC476470
0.6322	Remote Similarity	NPC136042
0.6316	Remote Similarity	NPC64425
0.6304	Remote Similarity	NPC251417
0.6263	Remote Similarity	NPC602448
0.6262	Remote Similarity	NPC209550
0.6207	Remote Similarity	NPC289667
0.6207	Remote Similarity	NPC238376
0.6162	Remote Similarity	NPC470449
0.6122	Remote Similarity	NPC486577
0.6061	Remote Similarity	NPC470447
0.6023	Remote Similarity	NPC127546
0.6023	Remote Similarity	NPC57625
0.6023	Remote Similarity	NPC19709
0.6023	Remote Similarity	NPC173637
0.6023	Remote Similarity	NPC317489
0.6023	Remote Similarity	NPC223424
0.6023	Remote Similarity	NPC600591
0.6022	Remote Similarity	NPC116864
0.6022	Remote Similarity	NPC244776
0.602	Remote Similarity	NPC122467
0.602	Remote Similarity	NPC606657
0.6019	Remote Similarity	NPC292019
0.6019	Remote Similarity	NPC202908
0.6	Remote Similarity	NPC298171
0.6	Remote Similarity	NPC275454
0.5979	Remote Similarity	NPC488073
0.5979	Remote Similarity	NPC488074
0.5979	Remote Similarity	NPC64051
0.5938	Remote Similarity	NPC479405
0.5918	Remote Similarity	NPC65711
0.5905	Remote Similarity	NPC277532
0.59	Remote Similarity	NPC89127
0.5895	Remote Similarity	NPC187379
0.5889	Remote Similarity	NPC84362
0.5889	Remote Similarity	NPC27640
0.5876	Remote Similarity	NPC129264
0.5876	Remote Similarity	NPC479404
0.5818	Remote Similarity	NPC138990
0.5816	Remote Similarity	NPC470125
0.5789	Remote Similarity	NPC483159
0.5789	Remote Similarity	NPC483160
0.5766	Remote Similarity	NPC175429
0.5745	Remote Similarity	NPC476215
0.5743	Remote Similarity	NPC85751
0.5743	Remote Similarity	NPC19240
0.5728	Remote Similarity	NPC470455
0.5714	Remote Similarity	NPC204693
0.57	Remote Similarity	NPC473623
0.57	Remote Similarity	NPC270448
0.5688	Remote Similarity	NPC298666
0.5673	Remote Similarity	NPC89052
0.5667	Remote Similarity	NPC77672
0.5667	Remote Similarity	NPC133671
0.5667	Remote Similarity	NPC135391
0.5667	Remote Similarity	NPC78263
0.5667	Remote Similarity	NPC250069
0.5657	Remote Similarity	NPC153755
0.5652	Remote Similarity	NPC59534
0.5644	Remote Similarity	NPC270675
0.5644	Remote Similarity	NPC488089
0.5644	Remote Similarity	NPC195685
0.5638	Remote Similarity	NPC223747
0.5636	Remote Similarity	NPC474522
0.5631	Remote Similarity	NPC470446
0.5604	Remote Similarity	NPC323593
0.5604	Remote Similarity	NPC203500
0.56	Remote Similarity	NPC479403
0.5588	Remote Similarity	NPC80068
0.5579	Remote Similarity	NPC66087
0.5577	Remote Similarity	NPC214621
0.5577	Remote Similarity	NPC34267
0.5566	Remote Similarity	NPC173837
0.5556	Remote Similarity	NPC473043
0.5556	Remote Similarity	NPC135599
0.5556	Remote Similarity	NPC73855
0.5556	Remote Similarity	NPC113968
0.5556	Remote Similarity	NPC328940
0.5556	Remote Similarity	NPC277174
0.5556	Remote Similarity	NPC606877
0.5545	Remote Similarity	NPC229409
0.5543	Remote Similarity	NPC305811
0.5543	Remote Similarity	NPC24043
0.5536	Remote Similarity	NPC241781
0.5534	Remote Similarity	NPC292929
0.5534	Remote Similarity	NPC470445
0.5524	Remote Similarity	NPC11468
0.5521	Remote Similarity	NPC265115
0.5514	Remote Similarity	NPC303694
0.5514	Remote Similarity	NPC164704
0.551	Remote Similarity	NPC163242
0.551	Remote Similarity	NPC272068
0.5495	Remote Similarity	NPC39360
0.5495	Remote Similarity	NPC29763
0.5495	Remote Similarity	NPC210003
0.5495	Remote Similarity	NPC348541
0.5487	Remote Similarity	NPC192539
0.5484	Remote Similarity	NPC27942
0.5481	Remote Similarity	NPC470450
0.5481	Remote Similarity	NPC472994
0.5481	Remote Similarity	NPC135358
0.5455	Remote Similarity	NPC473512
0.5455	Remote Similarity	NPC65003
0.5455	Remote Similarity	NPC129827
0.5455	Remote Similarity	NPC605592
0.5437	Remote Similarity	NPC471669
0.5435	Remote Similarity	NPC265530
0.5426	Remote Similarity	NPC219904
0.5408	Remote Similarity	NPC139320
0.5408	Remote Similarity	NPC609888
0.5405	Remote Similarity	NPC480445
0.5393	Remote Similarity	NPC54802
0.5393	Remote Similarity	NPC197304
0.5385	Remote Similarity	NPC473554
0.5385	Remote Similarity	NPC36138
0.5375	Remote Similarity	NPC146679
0.5357	Remote Similarity	NPC156785
0.5357	Remote Similarity	NPC162394
0.5333	Remote Similarity	NPC288084
0.5333	Remote Similarity	NPC223426
0.5326	Remote Similarity	NPC476405
0.5315	Remote Similarity	NPC488739
0.531	Remote Similarity	NPC470720
0.5294	Remote Similarity	NPC483414
0.5294	Remote Similarity	NPC483415
0.5278	Remote Similarity	NPC480796
0.5278	Remote Similarity	NPC472993
0.5273	Remote Similarity	NPC470716

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC50759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5435
0.1-0.2	3661
0.2-0.3	46
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
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
0.8068	Intermediate Similarity	NPD7251	Phase 2
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.734	Intermediate Similarity	NPD7808	Phase 3
0.6702	Remote Similarity	NPD7054	Phase 4
0.5234	Remote Similarity	NPD7472	Pre-clinical

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