NPASS Compound

Natural Product: NPC83743

Natural Product ID	NPC83743
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CZRAPNGXDBHAHC-SOUWYMHNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581235
PubChem CID	NA
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 87 90 0 0 0 0 0 0 0 0999 V2000 -8.6101 5.1474 -2.2391 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9854 4.2650 -3.2806 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4983 2.9629 -3.3560 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6166 2.4477 -2.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1087 1.1720 -2.4552 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1684 0.6599 -1.4699 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6817 1.3304 -0.4554 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7280 0.7214 0.4933 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3111 1.4345 1.4280 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2883 -0.5770 0.3876 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3727 -1.2003 1.2566 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0154 -0.4907 1.2093 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1332 -1.1007 2.0738 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1544 -1.2994 1.4721 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9804 -1.6452 2.4629 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5225 -2.8674 2.5793 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5313 -3.9764 2.8704 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4291 -4.1261 1.9055 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3305 -2.8256 3.7471 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3045 -3.7603 3.6043 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4400 -4.1563 2.1874 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4573 -3.1958 1.4850 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2351 -2.0898 1.1132 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4732 -1.7539 -0.2179 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9760 -2.4709 -1.0931 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2961 -0.5736 -0.5084 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8099 0.1739 0.4500 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6277 1.3482 0.2672 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 2.0317 1.3643 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8822 3.1753 1.2103 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1988 3.6092 -0.0580 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7464 2.9359 -1.1715 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9552 1.7982 -0.9832 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0899 3.4085 -2.4277 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6742 2.7853 -3.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9937 4.7541 -0.1699 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1159 -5.4813 1.9135 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6217 -3.1104 4.0521 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6843 -3.9852 3.9450 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4894 0.0414 0.8757 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2288 0.1051 -0.4602 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5845 -0.5568 -0.2407 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4913 0.1953 -0.9816 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4620 -0.6930 -1.3631 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0793 1.0910 1.7050 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5308 0.3578 -3.5136 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4054 0.8391 -4.4544 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8922 2.1376 -4.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7722 2.5428 -5.3755 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1971 6.0814 -2.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7790 4.6330 -1.2826 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5138 5.3438 -2.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3155 3.0999 -1.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8276 -0.3692 -1.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9975 2.3544 -0.3250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1995 -2.2433 0.9267 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7758 -1.2152 2.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1786 0.5449 1.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0454 -2.0148 0.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1347 -3.7819 3.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1082 -4.9192 2.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0319 -4.6793 1.1633 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1866 -4.6449 4.2760 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4420 -3.9686 1.7870 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0200 -3.7207 0.6033 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5028 -0.2860 -1.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5627 -0.1727 1.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8568 1.7161 2.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2191 3.6786 2.1109 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6380 1.3251 -1.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2172 3.1759 -4.4972 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5866 2.9900 -3.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7909 1.6973 -3.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0504 5.4319 0.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3554 -6.0073 2.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8070 -2.1717 3.4826 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4415 -2.7861 5.1061 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5070 -3.4343 3.8299 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5788 0.1081 0.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3086 1.1118 -0.8658 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6087 -1.5994 -0.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6090 -0.1923 -1.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2249 -1.6415 -1.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4449 1.9423 1.4158 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1289 -0.6483 -3.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7324 0.2001 -5.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7935 3.5265 -5.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 16 15 1 6 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 31 36 1 0 21 37 1 0 20 38 1 0 38 39 1 0 14 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 5 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 48 3 1 0 42 12 1 0 22 16 1 0 33 28 1 0 1 50 1 0 1 51 1 0 1 52 1 0 4 53 1 0 6 54 1 0 7 55 1 0 11 56 1 0 11 57 1 0 12 58 1 1 14 59 1 6 17 60 1 0 17 61 1 0 18 62 1 0 20 63 1 1 21 64 1 6 22 65 1 6 26 66 1 0 27 67 1 0 29 68 1 0 30 69 1 0 33 70 1 0 35 71 1 0 35 72 1 0 35 73 1 0 36 74 1 0 37 75 1 0 38 76 1 0 38 77 1 0 39 78 1 0 40 79 1 6 41 80 1 6 42 81 1 6 43 82 1 0 44 83 1 0 45 84 1 0 46 85 1 0 47 86 1 0 49 87 1 0 M END

Standard InCHIKey	CZRAPNGXDBHAHC-SOUWYMHNSA-N
Standard InCHI	InChI=1S/C32H38O17/c1-43-20-11-16(3-7-18(20)35)5-9-24(37)45-14-23-26(39)28(41)29(42)31(46-23)49-32(15-34)30(27(40)22(13-33)48-32)47-25(38)10-6-17-4-8-19(36)21(12-17)44-2/h3-12,22-23,26-31,33-36,39-42H,13-15H2,1-2H3/b9-5+,10-6+/t22-,23-,26-,27-,28+,29-,30+,31-,32+/m1/s1
SMILES	COc1cc(/C=C/C(=O)OC[C@H]2O[C@H](O[C@]3(CO)O[C@@H]([C@H]([C@@H]3OC(=O)/C=C/c3ccc(c(c3)OC)O)O)CO)[C@@H]([C@H]([C@@H]2O)O)O)ccc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	694.21	Volume:	650.871 ? Van der Waals volume.
Dense:	1.067	LogP:	1.188 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.534 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.847 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	27.0
TPSA:	260.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.088	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.872	Fsp³:	0.438
MCE-18:	105.13 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.777	Fluc inhibitor:	0.672 ? 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:	0.648 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.134	Promiscuous compounds:	0.296

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.306	MDCK Permeability:	-5.491
Pgp-inhibitor:	0.0	Pgp-substrate:	0.238
PAMPA:	0.99 ? 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):	0.976
20% Bioavailability (F20%):	0.998	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):	70.181%	Volume Distribution (VD):	-0.385
Fu:	27.192% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.107
BSEP inhibitor:	0.064

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.033 ? 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):

1.918

Half-life (T1/2):

2.417

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.095
Human Hepatotoxicity (H-HT):	0.484	Drug-induced Liver Injury (DILI):	0.763
AMES Toxicity:	0.971	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.074	Skin Sensitization:	1.0
Carcinogencity:	0.196	Eye Corrosion:	0.0
Eye Irritation:	0.111	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.907
Hematotoxicity:	0.244	Drug-induced Nephrotoxicity:	0.946
Genotoxicity:	0.213	RPMI-8226 Immunitoxicity:	0.385
A549 Cytotoxicity:	0.794	Hek293 Cytotoxicity:	0.677
BCF:	0.605 ? 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:	3.23 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.071 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.19 ? 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
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711347]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18771240]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24176362]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25466198]
NPO3457	Streptomyces diastaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8904845]
NPO11115	Aspilia mossambicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3457	Streptomyces diastaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16807	Cyclamen purpurascens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5811	Pityrodia lepidota	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20448	Trifolium caucasicum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21508	Tilia tomentosa	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16807	Cyclamen purpurascens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5811	Pityrodia lepidota	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20448	Trifolium caucasicum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14775	Eupenicillium javanicum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16807	Cyclamen purpurascens	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6135	Ehretia philippinensis	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21453	Variolaria amara	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20313	Crotalus mitchellii	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11115	Aspilia mossambicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11816.1	Vigna unguiculata subsp. unguiculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19342	Bryocladia cuspidata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21508	Tilia tomentosa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3457	Streptomyces diastaticus	Species	Streptomycetaceae	Bacteria	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
IC50	5

Activity Type	# Activity
Cell line	5

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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	45500.0	nM	PMID[25466198]
NPT81	Cell line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[25466198]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	20030.0	nM	PMID[25466198]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	=	27920.0	nM	PMID[25466198]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	17750.0	nM	PMID[25466198]

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 NPC83743 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	13805
0.1-0.2	30425
0.2-0.3	4508
0.3-0.4	891
0.4-0.5	163
0.5-0.6	32
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.859	High Similarity	NPC262182
0.8571	High Similarity	NPC90896
0.85	High Similarity	NPC300262
0.8049	Intermediate Similarity	NPC283839
0.775	Intermediate Similarity	NPC226005
0.7625	Intermediate Similarity	NPC472612
0.75	Intermediate Similarity	NPC80732
0.7471	Intermediate Similarity	NPC472611
0.7241	Intermediate Similarity	NPC125823
0.7241	Intermediate Similarity	NPC7145
0.7241	Intermediate Similarity	NPC143480
0.7241	Intermediate Similarity	NPC173343
0.7089	Intermediate Similarity	NPC297342
0.7045	Intermediate Similarity	NPC287615
0.7045	Intermediate Similarity	NPC199311
0.7	Intermediate Similarity	NPC201148
0.6966	Remote Similarity	NPC3460
0.6897	Remote Similarity	NPC216819
0.6829	Remote Similarity	NPC225307
0.6739	Remote Similarity	NPC261122
0.6667	Remote Similarity	NPC289967
0.6477	Remote Similarity	NPC476865
0.6444	Remote Similarity	NPC192763
0.625	Remote Similarity	NPC476868
0.619	Remote Similarity	NPC219677
0.617	Remote Similarity	NPC210611
0.6136	Remote Similarity	NPC476869
0.6026	Remote Similarity	NPC157554
0.5979	Remote Similarity	NPC28651
0.5909	Remote Similarity	NPC471405
0.5795	Remote Similarity	NPC291296
0.5752	Remote Similarity	NPC601579
0.573	Remote Similarity	NPC28637
0.5729	Remote Similarity	NPC85192
0.567	Remote Similarity	NPC215095
0.5579	Remote Similarity	NPC11411
0.551	Remote Similarity	NPC600370
0.5495	Remote Similarity	NPC476864
0.5444	Remote Similarity	NPC156692
0.5435	Remote Similarity	NPC476866
0.5432	Remote Similarity	NPC307110
0.5385	Remote Similarity	NPC476867
0.5376	Remote Similarity	NPC488082
0.5368	Remote Similarity	NPC479767
0.5326	Remote Similarity	NPC157816
0.5312	Remote Similarity	NPC488081
0.5288	Remote Similarity	NPC479771
0.5269	Remote Similarity	NPC173150
0.5233	Remote Similarity	NPC229784
0.5222	Remote Similarity	NPC252833
0.5213	Remote Similarity	NPC471881
0.5204	Remote Similarity	NPC133984
0.5176	Remote Similarity	NPC470572
0.5138	Remote Similarity	NPC484988
0.5109	Remote Similarity	NPC10205
0.5086	Remote Similarity	NPC246024
0.5056	Remote Similarity	NPC157898
0.5053	Remote Similarity	NPC21516
0.5051	Remote Similarity	NPC229548
0.5043	Remote Similarity	NPC25946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC83743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4394
0.1-0.2	4614
0.2-0.3	135
0.3-0.4	6
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