NPASS Compound

Natural Product: NPC56362

Natural Product ID	NPC56362
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IQBMWEYFKNVACH-MEBVLIOMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5282167
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 95100 0 0 0 0 0 0 0 0999 V2000 4.1651 1.3072 2.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5617 1.8405 4.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2908 2.3619 4.0057 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6468 2.3323 2.7973 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2678 1.7886 1.6589 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5251 1.2667 1.6896 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2410 0.7425 0.5424 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6432 0.3938 -0.6130 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4375 -0.0977 -1.6534 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9724 -0.4411 -2.7560 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7865 -0.1953 -1.4208 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6261 -0.6764 -2.4096 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9928 -0.7876 -2.2030 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5585 -0.4186 -0.9961 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7280 0.0633 -0.0014 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3579 0.1693 -0.2234 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5741 0.6209 0.7085 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9169 -0.5188 -0.7665 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0567 -1.0454 -3.6170 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2822 0.4581 -0.8978 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4461 -0.6825 -0.6925 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0925 -0.2988 -0.2904 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5193 0.6469 -1.2950 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0803 0.2760 -2.6648 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4891 -1.1015 -2.7827 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0441 -1.2112 -4.2112 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5513 -2.4582 -4.4882 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5062 -1.3679 -1.9188 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1531 0.3884 -3.5715 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3062 1.9893 -0.9921 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7975 -1.3774 -0.2063 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3838 -1.5211 1.0442 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8856 -1.3710 0.9679 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5334 -2.6012 1.5814 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9280 -3.8405 0.9063 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4829 -3.8569 1.3116 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6788 -4.6399 0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5715 -3.8991 -0.8743 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9456 -2.6676 1.6674 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6405 -4.9268 1.4402 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8978 -2.6505 1.3413 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2485 -0.2338 1.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9957 0.6711 0.8987 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2698 0.9378 1.6694 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6118 2.4130 1.6572 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4587 2.8726 0.2043 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0212 2.6314 -0.2088 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3931 3.9733 -0.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1426 4.6140 -1.4403 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3298 1.9096 0.7758 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3410 2.0828 -0.5370 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7558 3.1008 2.4962 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3083 0.1529 1.2086 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3655 2.8524 2.7211 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6857 2.9004 5.1464 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1710 0.9040 3.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0532 1.8713 5.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7395 1.8127 0.7366 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6350 -1.1753 -3.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1442 0.3593 0.9571 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2137 -0.8524 0.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4891 -1.7009 -4.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0149 -1.3497 0.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0998 0.1605 0.7214 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6489 0.5246 -1.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7010 1.0055 -2.9965 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2693 -1.9029 -2.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8038 -0.4525 -4.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2238 -1.0328 -4.9506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3364 -2.7120 -3.9372 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4343 -0.5004 -3.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2688 2.3580 -1.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9491 -0.6674 1.6561 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2548 -1.3665 -0.0983 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3554 -2.6930 2.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0954 -3.8143 -0.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4546 -4.5099 2.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2340 -5.5722 0.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3052 -4.9681 0.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9772 -4.3269 -1.6692 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2763 -5.3190 0.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1781 -3.4448 0.8362 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1874 0.3374 -0.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1188 0.6728 2.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6395 2.5149 2.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7554 3.9293 0.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0306 2.0764 -1.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4699 4.6117 0.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3400 3.8902 -0.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8801 5.5311 -1.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1904 2.5883 -0.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0668 2.5190 2.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1741 0.6119 1.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1168 3.3052 1.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5328 3.9061 5.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 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 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 45 52 1 0 44 53 1 0 4 54 1 0 3 55 1 0 6 1 1 0 17 7 1 0 28 21 1 0 39 32 1 0 50 43 1 0 16 11 1 0 1 56 1 0 2 57 1 0 5 58 1 0 13 59 1 0 15 60 1 0 18 61 1 0 19 62 1 0 21 63 1 1 22 64 1 1 23 65 1 6 24 66 1 6 25 67 1 6 26 68 1 0 26 69 1 0 27 70 1 0 29 71 1 0 30 72 1 0 32 73 1 1 33 74 1 6 34 75 1 1 35 76 1 6 36 77 1 1 37 78 1 0 37 79 1 0 38 80 1 0 40 81 1 0 41 82 1 0 43 83 1 6 44 84 1 1 45 85 1 1 46 86 1 1 47 87 1 6 48 88 1 0 48 89 1 0 49 90 1 0 51 91 1 0 52 92 1 0 53 93 1 0 54 94 1 0 55 95 1 0 M END

Standard InCHIKey	IQBMWEYFKNVACH-MEBVLIOMSA-N
Standard InCHI	InChI=1S/C33H40O22/c34-6-15-19(41)23(45)26(48)31(50-15)54-29-24(46)20(42)17(8-36)52-33(29)55-30-25(47)21(43)16(7-35)51-32(30)53-28-22(44)18-13(40)4-10(37)5-14(18)49-27(28)9-1-2-11(38)12(39)3-9/h1-5,15-17,19-21,23-26,29-43,45-48H,6-8H2/t15-,16-,17-,19-,20-,21-,23+,24+,25+,26-,29-,30-,31+,32+,33+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	788.2	Volume:	700.279 ? Van der Waals volume.
Dense:	1.126	LogP:	-1.863 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.363 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.796 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	368.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	14.0	Rings:	6.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.421	Fsp³:	0.545
MCE-18:	154.294 ? 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:	0.637	Fluc inhibitor:	0.303 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.695 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.638 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.529	Promiscuous compounds:	0.638

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.001	MDCK Permeability:	-4.783
Pgp-inhibitor:	0.0	Pgp-substrate:	0.48
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):	0.999
20% Bioavailability (F20%):	0.82	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.008
Plasma Protein Binding (PPB):	77.768%	Volume Distribution (VD):	-0.154
Fu:	22.092% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.304
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:	0.041
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.883
HLM stability:	0.005 ? 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):

1.033

Half-life (T1/2):

5.251

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.678	Drug-induced Liver Injury (DILI):	0.969
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.06	Eye Corrosion:	0.0
Eye Irritation:	0.066	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.087	Drug-induced Nephrotoxicity:	0.386
Genotoxicity:	0.936	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.94	Hek293 Cytotoxicity:	0.58
BCF:	0.285 ? 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:	2.612 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.342 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.425 ? 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
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15286289]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[20947202]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253552]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Wax	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11043	Pisum sativum	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 NPC56362 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	25996
0.1-0.2	19709
0.2-0.3	3293
0.3-0.4	436
0.4-0.5	204
0.5-0.6	98
0.6-0.7	75
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC254855
0.9351	High Similarity	NPC94610
0.8659	High Similarity	NPC155877
0.85	High Similarity	NPC170052
0.85	High Similarity	NPC135846
0.8118	Intermediate Similarity	NPC255157
0.8118	Intermediate Similarity	NPC259896
0.7882	Intermediate Similarity	NPC163242
0.7882	Intermediate Similarity	NPC272068
0.7738	Intermediate Similarity	NPC95866
0.7386	Intermediate Similarity	NPC304741
0.7317	Intermediate Similarity	NPC145038
0.7317	Intermediate Similarity	NPC56077
0.7317	Intermediate Similarity	NPC281131
0.7317	Intermediate Similarity	NPC253662
0.7317	Intermediate Similarity	NPC179950
0.7317	Intermediate Similarity	NPC88789
0.7317	Intermediate Similarity	NPC491374
0.7283	Intermediate Similarity	NPC220173
0.7273	Intermediate Similarity	NPC470405
0.7253	Intermediate Similarity	NPC122467
0.7159	Intermediate Similarity	NPC29958
0.7128	Intermediate Similarity	NPC602448
0.7079	Intermediate Similarity	NPC471748
0.7021	Intermediate Similarity	NPC292929
0.7011	Intermediate Similarity	NPC476215
0.7	Intermediate Similarity	NPC156869
0.6915	Remote Similarity	NPC76831
0.6848	Remote Similarity	NPC253521
0.6848	Remote Similarity	NPC113836
0.6837	Remote Similarity	NPC219043
0.6782	Remote Similarity	NPC224530
0.6747	Remote Similarity	NPC67037
0.6747	Remote Similarity	NPC255615
0.6636	Remote Similarity	NPC21359
0.6636	Remote Similarity	NPC460984
0.66	Remote Similarity	NPC303694
0.6596	Remote Similarity	NPC12013
0.6596	Remote Similarity	NPC11432
0.6596	Remote Similarity	NPC477613
0.6588	Remote Similarity	NPC77672
0.6588	Remote Similarity	NPC133671
0.6588	Remote Similarity	NPC135391
0.6588	Remote Similarity	NPC78263
0.6588	Remote Similarity	NPC250069
0.6562	Remote Similarity	NPC89127
0.6517	Remote Similarity	NPC136761
0.65	Remote Similarity	NPC48984
0.6484	Remote Similarity	NPC473682
0.6452	Remote Similarity	NPC605592
0.6413	Remote Similarity	NPC139320
0.6395	Remote Similarity	NPC127546
0.6395	Remote Similarity	NPC19388
0.6395	Remote Similarity	NPC240431
0.6395	Remote Similarity	NPC57625
0.6395	Remote Similarity	NPC55786
0.6395	Remote Similarity	NPC173637
0.6395	Remote Similarity	NPC317489
0.6395	Remote Similarity	NPC223424
0.6395	Remote Similarity	NPC600591
0.6392	Remote Similarity	NPC473071
0.6383	Remote Similarity	NPC470444
0.6354	Remote Similarity	NPC35119
0.6337	Remote Similarity	NPC292019
0.6337	Remote Similarity	NPC202908
0.6322	Remote Similarity	NPC64305
0.6316	Remote Similarity	NPC61904
0.6316	Remote Similarity	NPC240306
0.6292	Remote Similarity	NPC60735
0.6292	Remote Similarity	NPC26230
0.6238	Remote Similarity	NPC488075
0.6222	Remote Similarity	NPC120099
0.6186	Remote Similarity	NPC32641
0.6186	Remote Similarity	NPC256188
0.618	Remote Similarity	NPC472459
0.617	Remote Similarity	NPC67326
0.6168	Remote Similarity	NPC480444
0.6162	Remote Similarity	NPC221342
0.6162	Remote Similarity	NPC476470
0.6139	Remote Similarity	NPC89052
0.6129	Remote Similarity	NPC8856
0.6117	Remote Similarity	NPC480441
0.6111	Remote Similarity	NPC175107
0.6105	Remote Similarity	NPC203259
0.6105	Remote Similarity	NPC33054
0.6105	Remote Similarity	NPC176740
0.6105	Remote Similarity	NPC471725
0.6105	Remote Similarity	NPC134532
0.6105	Remote Similarity	NPC602582
0.6091	Remote Similarity	NPC25946
0.6087	Remote Similarity	NPC203050
0.6087	Remote Similarity	NPC225434
0.6082	Remote Similarity	NPC480471
0.6082	Remote Similarity	NPC488076
0.6075	Remote Similarity	NPC488740
0.6075	Remote Similarity	NPC488736
0.6075	Remote Similarity	NPC488733
0.6055	Remote Similarity	NPC192539
0.6047	Remote Similarity	NPC288084
0.6044	Remote Similarity	NPC609478
0.6	Remote Similarity	NPC249560
0.6	Remote Similarity	NPC470718
0.5963	Remote Similarity	NPC488737
0.5962	Remote Similarity	NPC470712
0.5882	Remote Similarity	NPC14187
0.5876	Remote Similarity	NPC35167
0.5862	Remote Similarity	NPC276222
0.5862	Remote Similarity	NPC274618
0.5862	Remote Similarity	NPC34531
0.5862	Remote Similarity	NPC118284
0.5862	Remote Similarity	NPC608147
0.5851	Remote Similarity	NPC116864
0.5851	Remote Similarity	NPC244776
0.5825	Remote Similarity	NPC203145
0.5824	Remote Similarity	NPC42773
0.5824	Remote Similarity	NPC216496
0.5824	Remote Similarity	NPC45522
0.5824	Remote Similarity	NPC325555
0.5824	Remote Similarity	NPC226304
0.5824	Remote Similarity	NPC599850
0.578	Remote Similarity	NPC162394
0.5778	Remote Similarity	NPC136042
0.5769	Remote Similarity	NPC189564
0.5743	Remote Similarity	NPC471669
0.573	Remote Similarity	NPC111929
0.573	Remote Similarity	NPC320283
0.573	Remote Similarity	NPC41121
0.5714	Remote Similarity	NPC115674
0.5702	Remote Similarity	NPC487499
0.5688	Remote Similarity	NPC480445
0.5688	Remote Similarity	NPC470713
0.566	Remote Similarity	NPC25523
0.5657	Remote Similarity	NPC488073
0.5657	Remote Similarity	NPC64425
0.5644	Remote Similarity	NPC97119
0.5596	Remote Similarity	NPC488734
0.5596	Remote Similarity	NPC488735
0.5596	Remote Similarity	NPC488739
0.5596	Remote Similarity	NPC488732
0.5596	Remote Similarity	NPC488738
0.5591	Remote Similarity	NPC235260
0.5591	Remote Similarity	NPC155763
0.5567	Remote Similarity	NPC471079
0.5566	Remote Similarity	NPC173837
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
0.5543	Remote Similarity	NPC52550
0.5543	Remote Similarity	NPC84362
0.5532	Remote Similarity	NPC259957
0.551	Remote Similarity	NPC173582
0.551	Remote Similarity	NPC265885
0.551	Remote Similarity	NPC181465
0.551	Remote Similarity	NPC215710
0.551	Remote Similarity	NPC473438
0.551	Remote Similarity	NPC253788
0.5508	Remote Similarity	NPC487502
0.5474	Remote Similarity	NPC605784
0.5426	Remote Similarity	NPC219904
0.5426	Remote Similarity	NPC488071
0.54	Remote Similarity	NPC144097
0.5392	Remote Similarity	NPC37668
0.5375	Remote Similarity	NPC286342
0.5368	Remote Similarity	NPC484158
0.5354	Remote Similarity	NPC39834
0.534	Remote Similarity	NPC142142
0.5328	Remote Similarity	NPC487500
0.5327	Remote Similarity	NPC473072
0.5312	Remote Similarity	NPC223747
0.53	Remote Similarity	NPC65003
0.5294	Remote Similarity	NPC297503
0.5294	Remote Similarity	NPC30011
0.5285	Remote Similarity	NPC487501
0.5269	Remote Similarity	NPC297987
0.5254	Remote Similarity	NPC473554
0.5253	Remote Similarity	NPC258044
0.5253	Remote Similarity	NPC217387
0.5243	Remote Similarity	NPC473327
0.5238	Remote Similarity	NPC33083
0.5238	Remote Similarity	NPC287889
0.5222	Remote Similarity	NPC54802
0.5222	Remote Similarity	NPC197304
0.5217	Remote Similarity	NPC476771
0.5213	Remote Similarity	NPC488080
0.5213	Remote Similarity	NPC169977
0.5196	Remote Similarity	NPC154741
0.5192	Remote Similarity	NPC603079
0.5189	Remote Similarity	NPC223426
0.5189	Remote Similarity	NPC253685
0.5161	Remote Similarity	NPC143851
0.5158	Remote Similarity	NPC21100
0.5149	Remote Similarity	NPC473862
0.5143	Remote Similarity	NPC476472
0.5143	Remote Similarity	NPC294815
0.5143	Remote Similarity	NPC16194
0.514	Remote Similarity	NPC81042
0.5106	Remote Similarity	NPC8573

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC56362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6505
0.1-0.2	2572
0.2-0.3	63
0.3-0.4	6
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6105	Remote Similarity	NPD6797	Phase 2

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