NPASS Compound

Natural Product: NPC141836

Natural Product ID	NPC141836
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SESLBPIXVOYQJJ-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	149044
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 78 78 0 0 0 0 0 0 0 0999 V2000 5.9278 -0.8758 -1.6315 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1572 -1.1265 -0.8146 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1789 -0.0779 -0.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9829 1.3140 -0.5551 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6715 1.8903 0.7208 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4463 1.7497 1.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9650 0.4485 1.9950 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7627 0.6726 2.9361 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6791 1.3519 2.1806 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4410 1.5704 3.0534 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9092 0.2516 3.5591 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5095 -0.6688 2.4122 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0137 -1.9379 3.0625 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6064 -2.9281 2.0119 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5092 -2.3429 1.1829 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9676 -3.3267 0.1140 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0883 -2.7232 -0.6661 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7458 -1.4391 -1.3774 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8417 -0.9197 -2.0942 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0451 -0.5197 -1.5668 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1576 -0.6416 -0.2962 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1708 0.0126 -2.2916 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2645 0.3535 -1.6476 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4415 0.8979 -2.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5084 1.0984 -3.6727 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6600 1.6212 -4.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7496 1.9498 -3.4994 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7214 1.7599 -2.1030 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5672 1.2419 -1.5746 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8484 2.1080 -1.3841 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9527 1.9784 -0.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9105 2.4729 -4.0510 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9648 0.1408 -2.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0162 -0.9885 -1.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8368 -1.6177 -2.4531 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8952 -1.5204 0.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6256 -2.0739 -1.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6319 -0.1650 -1.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0867 -0.4951 -0.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9668 1.8478 -0.9145 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2640 1.8234 -1.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5741 1.6123 1.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9110 3.0442 0.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4886 2.5161 2.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6242 2.2539 0.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7273 -0.1550 2.4703 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4736 -0.0582 1.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4040 -0.3323 3.2555 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1410 1.2254 3.8061 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4710 0.8273 1.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0096 2.4074 1.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6994 2.1998 3.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6758 2.0494 2.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9780 0.4659 4.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5957 -0.3004 4.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6987 -0.1521 1.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3320 -0.8955 1.7347 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0803 -1.7102 3.6583 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7695 -2.3555 3.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4613 -3.1869 1.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2516 -3.8696 2.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3681 -2.0202 1.7714 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1150 -1.4504 0.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4018 -4.1993 0.6829 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1555 -3.7230 -0.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0203 -2.6198 -0.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4235 -3.4278 -1.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4080 -0.6397 -0.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9485 -1.6310 -2.1448 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1156 0.1318 -3.3555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3231 0.2341 -0.5567 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6967 0.8661 -4.3216 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7166 1.7826 -5.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5140 1.0822 -0.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8994 1.4452 0.2967 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1526 1.4280 0.5073 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9502 2.9974 0.4894 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5467 1.9911 -4.6436 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 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 3 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 27 32 1 0 29 24 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 2 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 9 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 12 57 1 0 13 58 1 0 13 59 1 0 14 60 1 0 14 61 1 0 15 62 1 0 15 63 1 0 16 64 1 0 16 65 1 0 17 66 1 0 17 67 1 0 18 68 1 0 18 69 1 0 22 70 1 0 23 71 1 0 25 72 1 0 26 73 1 0 29 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 M END

Standard InCHIKey	SESLBPIXVOYQJJ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C28H46O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23-32-28(30)22-20-25-19-21-26(29)27(24-25)31-2/h19-22,24,29H,3-18,23H2,1-2H3
SMILES	CCCCCCCCCCCCCCCCCCOC(=O)C=Cc1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	446.34	Volume:	506.266 ? Van der Waals volume.
Dense:	0.882	LogP:	8.851 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.404 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.661 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	21.0	Rigid Bonds:	8.0
TPSA:	55.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.124	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.245	Fsp³:	0.679
MCE-18:	7.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.957	Fluc inhibitor:	0.999 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.196 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.7 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.747	Promiscuous compounds:	0.435

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.051	MDCK Permeability:	-4.803
Pgp-inhibitor:	0.001	Pgp-substrate:	0.008
PAMPA:	0.0 ? 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):	0.894
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.982
Plasma Protein Binding (PPB):	100.272%	Volume Distribution (VD):	1.23
Fu:	0.277% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.948
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.956
BSEP inhibitor:	0.866

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.354	CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.911	CYP2C9-substrate:	0.703
CYP2D6-inhibitor:	0.841	CYP2D6-substrate:	0.965
CYP3A4-inhibitor:	0.015	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.065	CYP2C8-inhibitor:	1.0
HLM stability:	0.23 ? 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):

4.72

Half-life (T1/2):

1.457

ADMET: Toxicity

hERG Blockers:	0.748	hERG Blockers (10um):	0.914
Human Hepatotoxicity (H-HT):	0.4	Drug-induced Liver Injury (DILI):	0.098
AMES Toxicity:	0.092	Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.297	Skin Sensitization:	0.999
Carcinogencity:	0.206	Eye Corrosion:	0.57
Eye Irritation:	0.982	Respiratory Toxicity:	0.887
Drug-induced Neurotoxicity:	0.047	Ototoxicity:	0.148
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	0.218
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.913	Hek293 Cytotoxicity:	0.539
BCF:	0.572 ? 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:	5.223 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.854 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.916 ? 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
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[32633512]
NPO822	Cressa cretica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11832	Pinus banksiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9311	Parkia clappertoniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9785	Dictyota binghamiae	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9051	Delesseria sanguinea	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7334	Embelia barbeyana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7334	Embelia barbeyana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7867	Cytisus caramanicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9785	Dictyota binghamiae	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10588	Diploschistes violarius	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO822	Cressa cretica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10775	Verbascum fruticulosum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5205	Gymnoascus reesii	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9311	Parkia clappertoniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7334	Embelia barbeyana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9051	Delesseria sanguinea	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28130	Neonotonia wightii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3007	Heliotropium bovei	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11832	Pinus banksiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10177	Eria linearifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12895	Polypodiodes niponica	Species	Polypodiaceae	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 NPC141836 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	8879
0.1-0.2	33275
0.2-0.3	6676
0.3-0.4	785
0.4-0.5	184
0.5-0.6	29
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC60517
1.0	High Similarity	NPC146886
1.0	High Similarity	NPC20443
0.9375	High Similarity	NPC83062
0.8491	Intermediate Similarity	NPC482462
0.7692	Intermediate Similarity	NPC70752
0.74	Intermediate Similarity	NPC202474
0.7115	Intermediate Similarity	NPC273741
0.7115	Intermediate Similarity	NPC608423
0.7115	Intermediate Similarity	NPC611337
0.6981	Remote Similarity	NPC203124
0.6981	Remote Similarity	NPC607366
0.6792	Remote Similarity	NPC246704
0.6727	Remote Similarity	NPC204466
0.6613	Remote Similarity	NPC475468
0.66	Remote Similarity	NPC107588
0.66	Remote Similarity	NPC137537
0.6538	Remote Similarity	NPC82731
0.6429	Remote Similarity	NPC110313
0.6393	Remote Similarity	NPC482043
0.6296	Remote Similarity	NPC328593
0.6102	Remote Similarity	NPC213552
0.6102	Remote Similarity	NPC120225
0.6	Remote Similarity	NPC280767
0.6	Remote Similarity	NPC135127
0.5926	Remote Similarity	NPC33749
0.5902	Remote Similarity	NPC110699
0.5902	Remote Similarity	NPC106055
0.5763	Remote Similarity	NPC15621
0.569	Remote Similarity	NPC289459
0.5667	Remote Similarity	NPC158949
0.5606	Remote Similarity	NPC481915
0.56	Remote Similarity	NPC36108
0.56	Remote Similarity	NPC233731
0.56	Remote Similarity	NPC610203
0.5556	Remote Similarity	NPC109275
0.5479	Remote Similarity	NPC484274
0.5373	Remote Similarity	NPC120852
0.537	Remote Similarity	NPC160900
0.5352	Remote Similarity	NPC158900
0.5283	Remote Similarity	NPC39793
0.5256	Remote Similarity	NPC132723
0.5256	Remote Similarity	NPC76032
0.5231	Remote Similarity	NPC485282
0.5231	Remote Similarity	NPC485283
0.5231	Remote Similarity	NPC485281
0.5185	Remote Similarity	NPC224814
0.5147	Remote Similarity	NPC471110
0.5139	Remote Similarity	NPC252402
0.5139	Remote Similarity	NPC102934
0.5132	Remote Similarity	NPC482415
0.5132	Remote Similarity	NPC482416
0.5088	Remote Similarity	NPC474967
0.5065	Remote Similarity	NPC274960

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141836 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2481
0.1-0.2	6203
0.2-0.3	450
0.3-0.4	12
0.4-0.5	3
0.5-0.6	1
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
0.537	Remote Similarity	NPD4379	Clinical (unspecified phase)

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