NPASS Compound

Natural Product: NPC184544

Natural Product ID	NPC184544
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QNGJHYZWDAADHI-HDCOVYJKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14188641
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins

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 69 72 0 0 0 0 0 0 0 0999 V2000 5.7818 2.5508 1.2279 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9165 1.6513 0.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1955 1.3468 -0.2205 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3039 1.9297 0.3884 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1552 2.8246 1.4186 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8842 3.1369 1.8409 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7512 4.0420 2.8819 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2634 3.4204 2.0423 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5730 1.6136 -0.0381 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7755 1.0276 -0.4601 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9613 0.2136 -1.4000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4681 1.2821 -0.1009 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3806 0.6571 -0.7579 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1106 1.1888 -0.0840 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1162 0.5280 -0.5786 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2404 1.5426 -0.5946 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8608 2.5683 -1.6666 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5571 3.0240 -1.3981 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3723 2.8539 -2.5289 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0936 2.5422 -0.2478 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7815 3.5855 -1.6489 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4944 0.9808 -0.8180 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5436 1.1042 0.0786 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3182 1.7578 1.1278 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8546 0.5142 -0.1595 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1506 -0.2099 -1.2920 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3754 -0.7751 -1.5394 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3872 -0.6103 -0.5904 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1143 0.1149 0.5589 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8516 0.6777 0.7778 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1177 0.2804 1.5039 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6241 -1.1814 -0.8410 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6373 -1.5064 -2.7070 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4659 -0.6745 0.0153 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5603 -1.9034 -0.6061 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3007 -1.8987 -1.8155 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9415 -3.1018 0.1397 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2234 -3.0686 1.4883 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5855 -4.2202 2.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6769 -5.4418 1.5520 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3948 -5.4750 0.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0339 -4.3249 -0.4890 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4808 -6.7013 -0.4586 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0386 -6.6027 2.2374 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8647 -4.1554 3.5473 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8048 2.8173 1.5828 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3076 0.6442 -1.0293 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3724 3.9380 3.6825 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8998 2.9104 2.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7513 0.7496 -0.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3631 0.8556 -1.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4524 -0.4404 -0.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2955 1.0185 1.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0695 0.2728 -1.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1755 2.0997 0.3815 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9067 2.0708 -2.6604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4842 4.1472 -1.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2733 3.5989 -3.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8484 4.0553 -2.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3714 -0.3376 -2.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6874 1.2430 1.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4606 1.1976 1.7797 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4730 -0.6780 -0.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5390 -1.3285 -3.1504 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1495 -2.1009 1.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8125 -4.3607 -1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7838 -7.4122 -0.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 -7.5109 1.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6969 -4.5580 3.9480 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 5 8 1 0 4 9 1 0 2 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 17 21 1 0 16 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 28 32 1 0 27 33 1 0 15 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 41 43 1 0 40 44 1 0 39 45 1 0 6 1 1 0 20 14 1 0 30 25 1 0 42 37 1 0 1 46 1 0 3 47 1 0 7 48 1 0 8 49 1 0 9 50 1 0 13 51 1 0 13 52 1 0 14 53 1 1 15 54 1 6 16 55 1 1 17 56 1 6 18 57 1 1 19 58 1 0 21 59 1 0 26 60 1 0 30 61 1 0 31 62 1 0 32 63 1 0 33 64 1 0 38 65 1 0 42 66 1 0 43 67 1 0 44 68 1 0 45 69 1 0 M END

Standard InCHIKey	QNGJHYZWDAADHI-HDCOVYJKSA-N
Standard InCHI	InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(38)42-7-17-22(44-25(39)9-3-13(30)19(35)14(31)4-9)23(21(37)27(41)43-17)45-26(40)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-37,41H,7H2/t17-,21-,22-,23-,27-/m1/s1
SMILES	c1c(cc(c(c1O)O)O)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O)O1)O)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.1	Volume:	567.909 ? Van der Waals volume.
Dense:	1.12	LogP:	0.169 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.236 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.701 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	27.0
TPSA:	310.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	11.0	Rings:	4.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.09	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.325	Fsp³:	0.222
MCE-18:	105.697 ? 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:	0.832	Fluc inhibitor:	0.138 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.315 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.591 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.568	Promiscuous compounds:	0.963

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.078	MDCK Permeability:	-4.74
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
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):	0.0
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	62.845%	Volume Distribution (VD):	-0.205
Fu:	27.657% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.974
BSEP inhibitor:	0.023

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.039 ? 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):

5.947

Half-life (T1/2):

3.04

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.978
Human Hepatotoxicity (H-HT):	0.028	Drug-induced Liver Injury (DILI):	0.975
AMES Toxicity:	0.738	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.685	Skin Sensitization:	1.0
Carcinogencity:	0.071	Eye Corrosion:	0.001
Eye Irritation:	0.986	Respiratory Toxicity:	0.03
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.148
BCF:	0.385 ? 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:	3.236 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.255 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.12 ? 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
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2008.08.002]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713399]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104491]
NPO28785	Lumbricus terrestris	Species	Lumbricidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1909513]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21375312]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO6382	Chlorocebus aethiops	Species	Cercopithecidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29533	Argusia argentea	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29145	Carya tonkinensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28867	Holocarpha obconica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29452	Plantago indica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1290	Trilisa odoratissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28828	Rana arvalis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28924	Spongilla lacustris	Species	Spongillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28785	Lumbricus terrestris	Species	Lumbricidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28924	Spongilla lacustris	Species	Spongillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29452	Plantago indica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28785	Lumbricus terrestris	Species	Lumbricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6382	Chlorocebus aethiops	Species	Cercopithecidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29145	Carya tonkinensis	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1290	Trilisa odoratissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28847	Plectranthus fruticosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26650	Terminalia chebula	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28867	Holocarpha obconica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29030	Zanthoxylum americanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28828	Rana arvalis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29533	Argusia argentea	Species	Heliotropiaceae	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 NPC184544 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	18004
0.1-0.2	30434
0.2-0.3	1207
0.3-0.4	131
0.4-0.5	52
0.5-0.6	20
0.6-0.7	9
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
0.7963	Intermediate Similarity	NPC488888
0.6731	Remote Similarity	NPC239019
0.6731	Remote Similarity	NPC247629
0.6545	Remote Similarity	NPC283806
0.6545	Remote Similarity	NPC238419
0.6364	Remote Similarity	NPC205037
0.6364	Remote Similarity	NPC3746
0.6296	Remote Similarity	NPC120621
0.6111	Remote Similarity	NPC142528
0.6078	Remote Similarity	NPC610546
0.5926	Remote Similarity	NPC229036
0.5818	Remote Similarity	NPC482667
0.566	Remote Similarity	NPC226738
0.5484	Remote Similarity	NPC175793
0.5484	Remote Similarity	NPC159913
0.5439	Remote Similarity	NPC114791
0.5439	Remote Similarity	NPC104222
0.5439	Remote Similarity	NPC210501
0.5439	Remote Similarity	NPC318826
0.5439	Remote Similarity	NPC141331
0.5385	Remote Similarity	NPC302170
0.5273	Remote Similarity	NPC12218
0.5273	Remote Similarity	NPC225036
0.5263	Remote Similarity	NPC75945
0.5179	Remote Similarity	NPC121573
0.5172	Remote Similarity	NPC44260
0.5167	Remote Similarity	NPC172419
0.5088	Remote Similarity	NPC190587
0.5088	Remote Similarity	NPC603485
0.5077	Remote Similarity	NPC291957

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC184544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5151
0.1-0.2	3946
0.2-0.3	51
0.3-0.4	1
0.4-0.5	1
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