NPASS Compound

Natural Product: NPC478340

Natural Product ID	NPC478340
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PWPHNKPUZMICJC-NUZQUGCJSA-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:0001586] Biflavonoids and polyflavonoids

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 99108 0 0 0 0 0 0 0 0999 V2000 7.9529 0.2908 0.1732 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1543 0.9171 -0.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3457 0.2578 0.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3182 -1.0558 0.5257 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1143 -1.6793 0.7954 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9066 -1.0104 0.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6056 -1.6753 0.9097 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9912 -2.2888 -0.3259 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2467 -1.2690 -1.1540 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2170 -0.6447 -0.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5046 -0.4754 1.0630 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5559 0.0988 1.8724 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3364 0.5030 1.3718 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0129 0.3481 0.0290 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7182 0.7745 -0.5470 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4103 -0.0751 -0.1639 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2490 -1.3118 0.3997 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3416 -2.1116 0.7367 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6110 -1.6752 0.5094 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8033 -0.4274 -0.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1873 0.0283 -0.2995 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8972 -0.6784 -1.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7131 -0.2739 -2.6882 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3445 -0.8842 -3.7684 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1924 -1.9353 -3.5617 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3971 -2.3616 -2.2736 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7541 -1.7372 -1.1912 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9796 -2.1870 0.1005 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0016 -1.7930 1.0767 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4912 -2.2887 2.3737 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6084 -3.6436 2.5645 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0654 -4.1759 3.7658 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4073 -3.3282 4.7840 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2938 -1.9817 4.6029 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8352 -1.4447 3.3976 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6397 -1.1059 5.6348 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8611 -3.8831 5.9738 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9233 -0.2837 1.0182 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1986 0.2643 0.8734 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7591 -2.3787 0.8038 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8170 -2.5382 -4.6375 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8839 0.7685 -2.9813 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6988 0.3640 -0.3927 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8099 1.6120 -0.9588 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9992 2.6502 -0.4854 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1407 3.8719 -1.3395 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1328 3.7096 -2.7115 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2602 4.8406 -3.4894 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3928 6.1077 -2.9105 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 6.2373 -1.5357 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2691 5.1015 -0.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5308 7.5112 -1.0041 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5181 7.2154 -3.7454 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4206 2.2083 -0.3797 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0919 2.9248 -1.4285 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0342 -1.7683 0.6348 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9973 -0.2328 -0.7413 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7497 -0.4271 -2.1180 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4457 1.0637 2.2325 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7202 -0.8614 1.6387 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1183 -3.2957 0.0697 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4956 -1.7620 0.7136 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5883 0.8369 -0.1828 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9966 0.8133 0.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1665 1.9507 -0.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0750 -2.7131 1.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8510 -2.5391 1.5963 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8052 -2.6889 -0.9456 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7042 -1.8230 -1.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8969 -0.5401 -1.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8027 0.2259 2.9361 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8304 0.6062 -1.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1882 -3.0793 1.1786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1971 1.1448 -0.4677 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1639 -0.5230 -4.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0621 -3.1950 -2.0435 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3546 -4.3826 1.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1578 -5.2560 3.9153 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7721 -0.3769 3.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9410 -0.7080 6.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8112 -4.2681 6.0697 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4387 0.1696 1.8799 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0506 1.2244 0.6076 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7027 -3.0379 -4.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4834 0.9799 -3.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4325 2.9506 0.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0282 2.7155 -3.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2524 4.6969 -4.5589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2764 5.2380 0.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1346 7.7554 -0.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1952 7.9229 -3.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9326 2.6619 0.5200 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1725 2.3371 -2.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1921 -2.3406 1.4740 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5059 -0.1510 -2.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5426 1.9403 2.7254 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8100 -3.2035 1.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5153 -2.7685 0.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0167 0.7052 -1.0995 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 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 1 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 29 38 1 0 38 39 1 0 29 40 1 0 25 41 1 0 23 42 1 0 20 43 2 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 50 52 1 0 49 53 1 0 45 54 1 0 54 55 1 0 17 56 1 0 14 57 2 0 57 58 1 0 13 59 1 0 11 60 1 0 8 61 1 0 4 62 1 0 3 63 1 0 6 1 1 0 60 7 1 0 57 10 1 0 54 15 1 0 43 16 1 0 51 46 1 0 40 19 1 0 38 21 1 0 27 22 1 0 35 30 1 0 1 64 1 0 2 65 1 0 5 66 1 0 7 67 1 1 8 68 1 6 9 69 1 0 9 70 1 0 12 71 1 0 15 72 1 6 18 73 1 0 21 74 1 6 24 75 1 0 26 76 1 0 31 77 1 0 32 78 1 0 35 79 1 0 36 80 1 0 37 81 1 0 38 82 1 1 39 83 1 0 41 84 1 0 42 85 1 0 45 86 1 1 47 87 1 0 48 88 1 0 51 89 1 0 52 90 1 0 53 91 1 0 54 92 1 1 55 93 1 0 56 94 1 0 58 95 1 0 59 96 1 0 61 97 1 0 62 98 1 0 63 99 1 0 M END

Standard InCHIKey	PWPHNKPUZMICJC-NUZQUGCJSA-N
Standard InCHI	InChI=1S/C45H36O18/c46-18-10-26(53)33-31(11-18)62-45(17-3-6-22(49)25(52)9-17)44(59)38(33)36-32(63-45)14-28(55)35-37(40(58)42(61-43(35)36)16-2-5-21(48)24(51)8-16)34-27(54)13-30-19(39(34)57)12-29(56)41(60-30)15-1-4-20(47)23(50)7-15/h1-11,13-14,29,37-38,40-42,44,46-59H,12H2/t29-,37-,38+,40+,41+,42+,44+,45-/m0/s1
SMILES	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc(c([C@H]3c4c(cc5c([C@H]6c7c(cc(cc7O[C@](c7ccc(c(c7)O)O)([C@@H]6O)O5)O)O)c4O[C@H](c4ccc(c(c4)O)O)[C@@H]3O)O)c2O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	864.19	Volume:	812.079 ? Van der Waals volume.
Dense:	1.064	LogP:	1.466 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.608 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.471 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	54.0
TPSA:	320.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	14.0	Rings:	10.0
Heavy Atoms:	18.0

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:	6.316	Fsp³:	0.2
MCE-18:	210.0 ? 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:	0.895	Fluc inhibitor:	0.044 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.522 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.64 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.574	Promiscuous compounds:	0.099

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.82	MDCK Permeability:	-4.754
Pgp-inhibitor:	0.0	Pgp-substrate:	0.066
PAMPA:	0.013 ? 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):	0.0
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.962
Plasma Protein Binding (PPB):	91.958%	Volume Distribution (VD):	0.216
Fu:	10.292% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.006
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.039	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

8.026

Half-life (T1/2):

5.882

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.956
Human Hepatotoxicity (H-HT):	0.992	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.766	Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.071	Respiratory Toxicity:	0.932
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.654
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.998
BCF:	1.211 ? 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:	3.987 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.401 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.672 ? 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
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	2007; 2008	DOI[10.1007/s11746-010-1589-7]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	cotyledon	n.a.	PMID[11283027]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[12670184]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[21348467]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22537213]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Peanut Skins	n.a.	n.a.	PMID[28231711]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36431807]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oil	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oils	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seeds	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	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
Inhibition	3

Activity Type	# Activity
Cell line	3

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
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	100.0	%	PMID[28231711]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	99.36	%	PMID[28231711]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	28.6	%	PMID[28231711]

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 NPC478340 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	28737
0.1-0.2	19663
0.2-0.3	1262
0.3-0.4	93
0.4-0.5	35
0.5-0.6	28
0.6-0.7	13
0.7-0.8	0
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8846	High Similarity	NPC478337
0.8846	High Similarity	NPC478338
0.875	High Similarity	NPC159526
0.8481	Intermediate Similarity	NPC78074
0.8333	Intermediate Similarity	NPC147743
0.8333	Intermediate Similarity	NPC4809
0.8333	Intermediate Similarity	NPC73517
0.8125	Intermediate Similarity	NPC86630
0.7821	Intermediate Similarity	NPC478616
0.7821	Intermediate Similarity	NPC478339
0.7763	Intermediate Similarity	NPC272552
0.7763	Intermediate Similarity	NPC226108
0.7763	Intermediate Similarity	NPC322899
0.7632	Intermediate Similarity	NPC226809
0.759	Intermediate Similarity	NPC106601
0.759	Intermediate Similarity	NPC151474
0.75	Intermediate Similarity	NPC212614
0.75	Intermediate Similarity	NPC205613
0.7432	Intermediate Similarity	NPC294558
0.7432	Intermediate Similarity	NPC18185
0.7432	Intermediate Similarity	NPC263940
0.7215	Intermediate Similarity	NPC46283
0.7215	Intermediate Similarity	NPC469944
0.7215	Intermediate Similarity	NPC134911
0.7195	Intermediate Similarity	NPC471404
0.7125	Intermediate Similarity	NPC44192
0.7079	Intermediate Similarity	NPC478617
0.65	Remote Similarity	NPC155564
0.641	Remote Similarity	NPC58190
0.641	Remote Similarity	NPC108811
0.641	Remote Similarity	NPC170103
0.641	Remote Similarity	NPC236202
0.641	Remote Similarity	NPC262911
0.641	Remote Similarity	NPC202742
0.6329	Remote Similarity	NPC246202
0.6329	Remote Similarity	NPC224161
0.6329	Remote Similarity	NPC46335
0.6329	Remote Similarity	NPC279406
0.6329	Remote Similarity	NPC486519
0.6	Remote Similarity	NPC82917
0.5957	Remote Similarity	NPC484331
0.5895	Remote Similarity	NPC12326
0.5814	Remote Similarity	NPC278548
0.5595	Remote Similarity	NPC313116
0.5595	Remote Similarity	NPC603340
0.5584	Remote Similarity	NPC178054
0.551	Remote Similarity	NPC484330
0.5506	Remote Similarity	NPC20050
0.5465	Remote Similarity	NPC70409
0.5465	Remote Similarity	NPC204770
0.5465	Remote Similarity	NPC600551
0.5465	Remote Similarity	NPC601980
0.5465	Remote Similarity	NPC602065
0.5465	Remote Similarity	NPC611024
0.5366	Remote Similarity	NPC96576
0.5341	Remote Similarity	NPC600630
0.5341	Remote Similarity	NPC607896
0.5341	Remote Similarity	NPC611369
0.5333	Remote Similarity	NPC261619
0.5333	Remote Similarity	NPC61477
0.5333	Remote Similarity	NPC78770
0.5333	Remote Similarity	NPC219876
0.5333	Remote Similarity	NPC126029
0.5333	Remote Similarity	NPC15658
0.5275	Remote Similarity	NPC306267
0.5149	Remote Similarity	NPC185231
0.5056	Remote Similarity	NPC211561
0.5053	Remote Similarity	NPC9309

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5917
0.1-0.2	3211
0.2-0.3	18
0.3-0.4	2
0.4-0.5	0
0.5-0.6	2
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
0.5333	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5333	Remote Similarity	NPD1613	Phase 4

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