NPASS Compound

Natural Product: NPC478829

Natural Product ID	NPC478829
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PIAOUESCKPROBJ-XNSLRSMDSA-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 88 93 0 0 0 0 0 0 0 0999 V2000 10.2868 1.4927 2.0086 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2616 1.8231 1.2573 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2863 1.5674 -0.1918 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6218 2.8582 -0.9047 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9605 1.0676 -0.7146 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5614 -0.2345 -0.0436 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2582 -0.6906 -0.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2099 -0.8580 0.1781 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3064 -0.5904 1.6261 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9417 -1.3075 -0.4323 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8584 -1.5254 -1.6483 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8545 -1.4767 0.3849 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6177 -1.8848 -0.0624 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9702 -0.9203 -1.0748 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9981 0.4187 -0.4390 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0361 1.3868 -0.9024 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0097 0.6828 -1.8209 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3591 -0.6429 -1.2124 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2304 -1.4709 -1.3747 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6018 -0.5289 0.1010 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6980 -1.0688 0.6735 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9799 -2.4982 0.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4578 -2.1337 0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0705 -0.7033 0.3495 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5988 -0.4603 -0.9911 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8905 -0.0340 -1.0431 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1182 -0.4096 -0.7147 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2825 -1.5317 -0.1562 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3367 0.3747 -0.9463 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2895 1.6143 -1.5333 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4585 2.3532 -1.7498 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6805 1.8533 -1.3788 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7319 0.6133 -0.7919 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5610 -0.1208 -0.5781 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5055 0.1994 1.4621 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3366 0.4896 2.1814 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6677 -0.7239 2.1874 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2743 -0.6845 2.7018 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5205 -1.6883 2.9856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7949 -1.8765 2.2281 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6725 -2.7655 2.7880 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3973 -0.5977 2.1761 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3588 0.5216 -3.0524 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7736 1.8125 0.2091 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2540 1.0107 -0.7356 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3063 0.6502 -0.4723 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1521 1.0303 1.5561 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3018 1.6653 3.0739 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3988 2.2852 1.7182 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7862 2.7018 -1.9979 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5145 3.3407 -0.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7776 3.5755 -0.7735 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0790 0.8519 -1.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1982 1.8399 -0.5765 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5051 -0.0617 1.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3628 -0.9642 -0.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2034 -0.8856 -1.6426 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3040 -0.6821 2.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0164 -1.2664 2.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6273 0.4751 1.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6230 -2.8714 -0.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8533 -1.9938 0.7377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6761 -0.8902 -1.9575 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0291 0.3310 0.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3957 2.2967 -1.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9190 1.3395 -1.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1420 -1.1860 -1.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5944 -3.1884 1.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8929 -3.0086 -0.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1199 -2.6928 0.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5070 -1.3395 -1.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9722 0.3248 -1.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3298 2.0307 -1.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4147 3.3225 -2.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6201 2.4116 -1.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7013 0.2256 -0.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6678 -1.0849 -0.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0120 1.1144 1.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3021 -0.7246 3.8264 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8002 -1.6647 2.4235 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6621 0.1333 2.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7770 -1.1443 3.9411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0200 -2.6098 3.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6002 -2.5447 2.4878 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4017 1.4028 -3.4939 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4086 2.6629 0.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1544 2.0096 -0.7892 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0455 0.0704 -1.2373 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 21 20 1 6 21 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 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 24 35 1 0 35 36 1 0 36 37 1 0 37 38 1 1 37 39 1 0 39 40 1 0 40 41 1 1 40 42 1 0 17 43 1 0 16 44 1 0 15 45 1 0 3 46 1 1 19 14 1 0 37 21 1 0 24 21 1 0 34 29 1 0 42 35 1 0 40 23 1 0 1 47 1 0 1 48 1 0 2 49 1 0 4 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 9 58 1 0 9 59 1 0 9 60 1 0 13 61 1 0 13 62 1 0 14 63 1 6 15 64 1 1 16 65 1 6 17 66 1 6 18 67 1 6 22 68 1 0 22 69 1 0 23 70 1 0 25 71 1 0 25 72 1 0 30 73 1 0 31 74 1 0 32 75 1 0 33 76 1 0 34 77 1 0 35 78 1 6 38 79 1 0 38 80 1 0 38 81 1 0 39 82 1 0 39 83 1 0 41 84 1 0 43 85 1 0 44 86 1 0 45 87 1 0 46 88 1 0 M END

Standard InCHIKey	PIAOUESCKPROBJ-XNSLRSMDSA-N
Standard InCHI	InChI=1S/C33H42O13/c1-5-29(3,39)13-9-10-18(2)25(37)41-15-20-22(34)23(35)24(36)27(43-20)44-33-14-21-31(33,17-42-26(38)19-11-7-6-8-12-19)28-45-30(33,4)16-32(21,40)46-28/h5-8,10-12,20-24,27-28,34-36,39-40H,1,9,13-17H2,2-4H3/b18-10+/t20-,21?,22-,23+,24-,27+,28-,29-,30+,31?,32-,33+/m1/s1
SMILES	C=C[C@](C)(CC/C=C(C)/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@]12CC3C2(COC(=O)c2ccccc2)[C@@H]2O[C@@]1(C)C[C@@]3(O)O2)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	646.26	Volume:	623.803 ? Van der Waals volume.
Dense:	1.036	LogP:	2.111 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.283 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.339 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	29.0
TPSA:	190.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	5.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.122	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.699	Fsp³:	0.636
MCE-18:	153.185 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.524	Fluc inhibitor:	0.051 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.182 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.058	Promiscuous compounds:	0.065

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.6	MDCK Permeability:	-5.091
Pgp-inhibitor:	0.002	Pgp-substrate:	0.05
PAMPA:	0.995 ? 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):	0.021
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.904
Plasma Protein Binding (PPB):	70.102%	Volume Distribution (VD):	-0.694
Fu:	39.043% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.852
BSEP inhibitor:	0.447

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.006
CYP2C9-inhibitor:	0.016	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.503 ? 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):

2.217

Half-life (T1/2):

2.014

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.3
Human Hepatotoxicity (H-HT):	0.278	Drug-induced Liver Injury (DILI):	0.107
AMES Toxicity:	0.369	Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.748	Skin Sensitization:	0.987
Carcinogencity:	0.141	Eye Corrosion:	0.0
Eye Irritation:	0.223	Respiratory Toxicity:	0.416
Drug-induced Neurotoxicity:	0.056	Ototoxicity:	0.845
Hematotoxicity:	0.048	Drug-induced Nephrotoxicity:	0.646
Genotoxicity:	0.521	RPMI-8226 Immunitoxicity:	0.183
A549 Cytotoxicity:	0.314	Hek293 Cytotoxicity:	0.686
BCF:	0.496 ? 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:	3.505 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.464 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.612 ? 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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	5
IC50	1

Activity Type	# Activity
Cell line	6

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	=	41.32	%	PMID[29741372]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	38.13	%	PMID[29741372]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	28.06	%	PMID[29741372]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	22.56	%	PMID[29741372]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	9.85	%	PMID[29741372]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[29741372]

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 NPC478829 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	12941
0.1-0.2	33128
0.2-0.3	3676
0.3-0.4	73
0.4-0.5	9
0.5-0.6	12
0.6-0.7	11
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
0.7614	Intermediate Similarity	NPC34066
0.7614	Intermediate Similarity	NPC190862
0.7234	Intermediate Similarity	NPC469398
0.7071	Intermediate Similarity	NPC478828
0.7053	Intermediate Similarity	NPC469396
0.7053	Intermediate Similarity	NPC469458
0.7053	Intermediate Similarity	NPC149002
0.6907	Remote Similarity	NPC80360
0.6813	Remote Similarity	NPC303429
0.6813	Remote Similarity	NPC56594
0.6796	Remote Similarity	NPC478826
0.6796	Remote Similarity	NPC478827
0.6632	Remote Similarity	NPC88176
0.6538	Remote Similarity	NPC469421
0.6505	Remote Similarity	NPC188217
0.6355	Remote Similarity	NPC469397
0.6176	Remote Similarity	NPC195114
0.6117	Remote Similarity	NPC148185
0.5918	Remote Similarity	NPC293568
0.5918	Remote Similarity	NPC161626
0.5859	Remote Similarity	NPC120012
0.578	Remote Similarity	NPC477617
0.56	Remote Similarity	NPC469422
0.5455	Remote Similarity	NPC469448
0.54	Remote Similarity	NPC469417
0.5189	Remote Similarity	NPC469420
0.5138	Remote Similarity	NPC260300
0.5094	Remote Similarity	NPC469419
0.5051	Remote Similarity	NPC478832
0.5049	Remote Similarity	NPC222102

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4656
0.1-0.2	4424
0.2-0.3	69
0.3-0.4	1
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