NPASS Compound

Natural Product: NPC312727

Natural Product ID	NPC312727
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZYDLAYCPLOHXHH-YHNAUUMRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	16164119
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable 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 2D 114120 0 0 0 0 0 0 0 0999 V2000 1.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0905 -5.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -7.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -8.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6491 -6.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8886 -7.6375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0525 -10.3174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8886 -10.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3886 -10.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1386 -6.3385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.6386 -8.9366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1386 -11.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7291 -9.4496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -10.7487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4902 -10.9315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7291 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -13.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7291 -14.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -14.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9791 -13.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4791 -13.3467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9791 -15.9448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -15.9448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0800 -8.4854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -8.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3228 -7.2875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -12.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -12.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -13.6816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -14.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6588 -15.1635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -16.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -17.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -18.8777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0800 -18.8777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -17.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0800 -16.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3300 -17.5787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -20.1768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 -20.1768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -13.6816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9200 -11.0835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -5.7092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 -3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6595 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -5.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9095 -5.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9095 -3.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4095 -3.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -4.4101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -7.0082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 -3.1471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0162 -4.2086 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6491 -4.2320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8574 -4.9469 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 -6.6734 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -9.1148 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6491 -9.1148 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1386 -11.5347 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1386 -6.3385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3886 -5.0395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3886 -7.6375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6386 -11.5347 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4791 -13.3467 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1318 -10.8498 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2291 -14.6458 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4791 -15.9448 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0211 -17.0238 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 -8.4854 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0688 -11.2664 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -17.5787 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 -14.9806 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0800 -18.8777 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0800 -21.4758 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -21.4758 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8340 -15.0624 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6700 -12.3825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8235 -7.0900 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6595 -1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -1.8121 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9095 -3.1111 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -7.0082 0.0000 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 20 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 26 30 1 0 25 31 1 0 17 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 37 43 1 0 16 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 51 53 1 0 53 54 1 0 54 55 2 0 54 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 59 60 1 0 60 61 2 0 60 62 1 0 59 63 1 0 58 64 1 0 50 65 1 0 49 66 1 0 15 67 1 0 67 68 1 0 68 69 2 0 68 70 1 0 70 71 2 0 71 72 1 0 72 73 2 0 73 74 1 0 74 75 2 0 74 76 1 0 73 77 1 0 72 78 1 0 6 1 1 0 19 14 1 0 28 23 1 0 40 35 1 0 52 47 1 0 61 56 1 0 75 70 1 0 1 79 1 0 3 80 1 0 7 81 1 0 8 82 1 0 9 83 1 0 13 84 1 0 13 85 1 0 14 86 1 6 15 87 1 1 16 88 1 6 17 89 1 1 18 90 1 6 24 91 1 0 28 92 1 0 29 93 1 0 30 94 1 0 31 95 1 0 36 96 1 0 40 97 1 0 41 98 1 0 42 99 1 0 43100 1 0 48101 1 0 52102 1 0 57103 1 0 61104 1 0 62105 1 0 63106 1 0 64107 1 0 65108 1 0 66109 1 0 71110 1 0 75111 1 0 76112 1 0 77113 1 0 78114 1 0 M END

Standard InCHIKey	ZYDLAYCPLOHXHH-YHNAUUMRSA-N
Standard InCHI	InChI=1S/C48H36O30/c49-20-1-14(2-21(50)33(20)60)42(66)72-13-32-39(75-44(68)16-5-24(53)35(62)25(54)6-16)40(76-46(70)19-11-30(59)38(65)31(12-19)73-43(67)15-3-22(51)34(61)23(52)4-15)41(77-45(69)17-7-26(55)36(63)27(56)8-17)48(74-32)78-47(71)18-9-28(57)37(64)29(58)10-18/h1-12,32,39-41,48-65H,13H2/t32-,39-,40+,41-,48+/m1/s1
SMILES	c1c(cc(c(c1O)O)O)C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)OC(=O)c1cc(c(c(c1)O)O)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1092.13	Volume:	979.3 ? Van der Waals volume.
Dense:	1.115	LogP:	0.618 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.131 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.001 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	48.0
TPSA:	510.94 ? Topological Polar Surface Area.	H-Bond Acceptor:	30.0
H-Bond Donor:	17.0	Rings:	7.0
Heavy Atoms:	30.0

MedChem Properties

QED Drug-Likeness Score:	0.034	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.155	Fsp³:	0.125
MCE-18:	178.37 ? 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:	0.998	Fluc inhibitor:	0.184 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.255 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.748	Promiscuous compounds:	0.971

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-8.337	MDCK Permeability:	-4.544
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
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%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	75.286%	Volume Distribution (VD):	-0.147
Fu:	12.451% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.854
OATP1B3 inhibitor:	0.806	BCRP inhibitor:	0.997
BSEP inhibitor:	0.036

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.995
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:	0.008 ? 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):

6.262

Half-life (T1/2):

4.631

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.999
Human Hepatotoxicity (H-HT):	0.003	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.659	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.911	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.977	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.22
BCF:	0.066 ? 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:	3.73 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.53 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.574 ? 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
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785416]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11223086]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520228]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14559084]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	Bay of Naples, Italy	n.a.	PMID[7714539]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO550	Callicarpa maingayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3119	Cephalaria uralensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15448	Chrysothamnus parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5541	Crotalaria aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7013	Dicoma capensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO762	Digitalis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8437	Encyothalia cliftonii	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4073	Geranium sylvaticum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26170	Haliclona mucosa	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5301	Haplophyllum ferganicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2174	Polysiphonia elongata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8909	Pteris radiata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7625	Scopolia hladnikiana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8773	Sonchus ortunoi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5301	Haplophyllum ferganicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4073	Geranium sylvaticum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26170	Haliclona mucosa	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6039	Aglaia laxiflora	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8909	Pteris radiata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3119	Cephalaria uralensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO762	Digitalis isabelliana	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5065	Cladonia fallax	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8437	Encyothalia cliftonii	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7381	Ircinia spinosula	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2174	Polysiphonia elongata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO550	Callicarpa maingayi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8621	Cylindrospermopsis raciborskii	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15448	Chrysothamnus parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9973	Euphorbia turczaninowii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5541	Crotalaria aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8773	Sonchus ortunoi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9207	Styrax ferrugineus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7625	Scopolia hladnikiana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7013	Dicoma capensis	Species	Asteraceae	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 NPC312727 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	22680
0.1-0.2	26189
0.2-0.3	817
0.3-0.4	101
0.4-0.5	33
0.5-0.6	23
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC149300
0.7586	Intermediate Similarity	NPC114791
0.7586	Intermediate Similarity	NPC104222
0.7586	Intermediate Similarity	NPC210501
0.7586	Intermediate Similarity	NPC318826
0.7586	Intermediate Similarity	NPC141331
0.6324	Remote Similarity	NPC43918
0.6324	Remote Similarity	NPC261411
0.6324	Remote Similarity	NPC190204
0.6232	Remote Similarity	NPC469651
0.6176	Remote Similarity	NPC47521
0.5854	Remote Similarity	NPC223534
0.5663	Remote Similarity	NPC97924
0.5595	Remote Similarity	NPC290289
0.5581	Remote Similarity	NPC187632
0.5581	Remote Similarity	NPC240200
0.5581	Remote Similarity	NPC488885
0.5488	Remote Similarity	NPC40078
0.5476	Remote Similarity	NPC483712
0.5476	Remote Similarity	NPC158214
0.5476	Remote Similarity	NPC214202
0.5455	Remote Similarity	NPC194439
0.5455	Remote Similarity	NPC33724
0.5422	Remote Similarity	NPC112211
0.5422	Remote Similarity	NPC254925
0.5217	Remote Similarity	NPC7839
0.5217	Remote Similarity	NPC488884
0.5217	Remote Similarity	NPC142291
0.5165	Remote Similarity	NPC116108
0.5161	Remote Similarity	NPC488887
0.5161	Remote Similarity	NPC488886
0.5054	Remote Similarity	NPC471091
0.5052	Remote Similarity	NPC260521
0.505	Remote Similarity	NPC174140

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC312727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4957
0.1-0.2	4170
0.2-0.3	21
0.3-0.4	2
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