NPASS Compound

Natural Product: NPC205796

Natural Product ID	NPC205796
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-Pinoresinol-4,4'-Di-O-Beta-D-Glucopyranoside
IUPAC Name	(2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL573785
PubChem CID	45482330
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

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 90 95 0 0 0 0 0 0 0 0999 V2000 -10.5218 3.3952 2.4403 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4622 2.4769 2.4653 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0235 2.2590 1.0362 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9717 1.3445 1.0502 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3629 1.2426 -0.2038 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7858 -0.0195 -0.3004 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4685 -0.2947 -0.5064 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4838 0.6371 -0.6219 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1604 0.2685 -0.8347 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8124 -1.0306 -0.9335 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8274 -1.9825 -0.8135 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -1.6576 -0.6028 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1398 -2.6097 -0.4863 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8044 -3.9798 -0.5859 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4490 -1.5705 -1.1680 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2977 -2.6692 -0.3298 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0442 -2.0723 0.9044 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0660 -1.0567 0.5719 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3316 -0.6647 -0.8042 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8877 -1.1210 -1.6063 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3413 -2.2350 -0.8935 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3216 -1.8238 0.4380 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5730 -1.0597 0.6521 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7104 0.0774 1.3766 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9438 0.6779 1.4788 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0920 0.1656 0.8597 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9457 -0.9844 0.1279 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7037 -1.5710 0.0378 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0385 -1.5700 -0.5310 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8705 -2.7493 -1.2826 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2518 0.8335 1.0259 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5326 0.6511 0.5727 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3631 0.4736 1.6871 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6777 0.2191 1.3072 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4848 0.1597 2.5911 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8339 -0.0933 2.3587 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2557 1.2873 0.4400 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3378 1.7267 -0.6693 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9712 1.9742 -0.0793 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0671 2.3763 -1.0391 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8502 2.9304 -1.1697 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4313 0.8353 -0.1531 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4160 1.3201 -1.3115 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6840 0.6836 -0.7448 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2138 1.7119 0.2646 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8443 2.7064 -0.4736 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3754 -0.4589 -0.0158 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6790 2.6178 -1.6976 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5098 3.9117 1.5920 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7876 1.4970 2.8781 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6075 2.8697 3.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6872 3.2407 0.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6163 2.0371 -0.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7053 1.6963 -0.5509 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4149 1.0191 -0.9219 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5861 -3.0406 -0.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1067 -4.2918 0.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7370 -4.6060 -0.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3971 -4.2429 -1.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4041 -1.8914 -2.2452 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9130 -1.5792 1.3489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6646 -2.8433 1.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0587 -0.2320 1.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5076 0.4132 -0.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5574 -1.4778 -2.6040 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 -0.3521 -1.6387 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2797 -2.6996 1.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8384 0.4901 1.8628 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0296 1.5939 2.0700 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6166 -2.4939 -0.5550 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7678 -2.9570 -1.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7336 -3.5864 -0.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0171 -2.6750 -2.0024 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7338 -0.1579 -0.1231 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7958 -0.7628 0.8134 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4234 1.1457 3.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0482 -0.5820 3.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9589 -0.6722 1.5563 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4768 2.1689 1.0830 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3144 1.0213 -1.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0873 2.6951 0.7552 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1413 3.3787 -1.0983 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1188 2.8713 -2.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2282 0.4554 -1.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0236 0.7681 -2.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4290 0.4579 -1.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9287 1.2134 0.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3594 2.2719 -1.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9704 -0.5521 0.7548 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7857 2.7025 -2.6904 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 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 10 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 1 0 21 22 1 0 22 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 29 30 1 0 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 37 42 1 0 5 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 45 3 1 0 12 7 1 0 19 15 1 0 28 23 1 0 39 32 1 0 22 18 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 6 5 53 1 6 8 54 1 0 9 55 1 0 11 56 1 0 14 57 1 0 14 58 1 0 14 59 1 0 15 60 1 6 17 61 1 0 17 62 1 0 18 63 1 1 19 64 1 1 20 65 1 0 20 66 1 0 22 67 1 1 24 68 1 0 25 69 1 0 28 70 1 0 30 71 1 0 30 72 1 0 30 73 1 0 32 74 1 6 34 75 1 6 35 76 1 0 35 77 1 0 36 78 1 0 37 79 1 1 38 80 1 6 39 81 1 1 40 82 1 0 41 83 1 0 42 84 1 0 43 85 1 6 44 86 1 6 45 87 1 1 46 88 1 0 47 89 1 0 48 90 1 0 M END

Standard InCHIKey	ZJSJQWDXAYNLNS-PETZUENDSA-N
Standard InCHI	InChI=1S/C32H42O16/c1-41-19-7-13(3-5-17(19)45-31-27(39)25(37)23(35)21(9-33)47-31)29-15-11-44-30(16(15)12-43-29)14-4-6-18(20(8-14)42-2)46-32-28(40)26(38)24(36)22(10-34)48-32/h3-8,15-16,21-40H,9-12H2,1-2H3/t15-,16-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30+,31-,32-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2ccc(cc2OC)[C@@H]2OC[C@@H]3[C@H]2CO[C@H]3c2ccc(c(c2)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	682.25	Volume:	635.514 ? Van der Waals volume.
Dense:	1.074	LogP:	-1.045 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.172 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.959 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	33.0
TPSA:	235.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.058	Fsp³:	0.625
MCE-18:	137.385 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.526	Fluc inhibitor:	0.139 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.071 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.041 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.162	Promiscuous compounds:	0.033

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.951	MDCK Permeability:	-5.124
Pgp-inhibitor:	0.0	Pgp-substrate:	0.354
PAMPA:	0.857 ? 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):	0.594
20% Bioavailability (F20%):	0.013	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.022
Plasma Protein Binding (PPB):	65.63%	Volume Distribution (VD):	-0.4
Fu:	34.398% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.039
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.067	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.259	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

0.982

Half-life (T1/2):

6.16

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.939	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.143	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.996
Hematotoxicity:	0.564	Drug-induced Nephrotoxicity:	0.963
Genotoxicity:	0.882	RPMI-8226 Immunitoxicity:	0.216
A549 Cytotoxicity:	0.479	Hek293 Cytotoxicity:	0.19
BCF:	0.817 ? 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:	3.283 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.726 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.916 ? 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
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18636777]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29244495]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	Bark	n.a.	n.a.	PMID[30520635]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36364129]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4421	Penicillium cyclopium	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3255	Lampranthus sociorum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5981	Achlys triphylla	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3415	Perymenium mendezii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO855	Elymnias thryallis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7464	Uruparia lanosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4421	Penicillium cyclopium	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5981	Achlys triphylla	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4952	Pertusaria amara	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3415	Perymenium mendezii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7616	Melanargia galathea	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3263	Thea sasanqua	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6844	Bulbophyllum protractum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3255	Lampranthus sociorum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2963	Diospyros glaucifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4117	Nauclea rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15597	Calystegia pubescens	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29287	Alectoria ochroleuca	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7770	Lactuca laciniata	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell line	1

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	IC50	>	300000.0	nM	PMID[18986199]

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 NPC205796 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	13525
0.1-0.2	31627
0.2-0.3	3617
0.3-0.4	762
0.4-0.5	238
0.5-0.6	46
0.6-0.7	20
0.7-0.8	0
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC276753
0.9815	High Similarity	NPC246947
0.8689	High Similarity	NPC286235
0.8548	High Similarity	NPC38041
0.8548	High Similarity	NPC22150
0.8548	High Similarity	NPC279298
0.7759	Intermediate Similarity	NPC95392
0.7759	Intermediate Similarity	NPC84013
0.7759	Intermediate Similarity	NPC55715
0.7759	Intermediate Similarity	NPC35877
0.7313	Intermediate Similarity	NPC471063
0.7286	Intermediate Similarity	NPC186316
0.7083	Intermediate Similarity	NPC478055
0.7077	Intermediate Similarity	NPC486102
0.7042	Intermediate Similarity	NPC486098
0.7015	Intermediate Similarity	NPC51328
0.7015	Intermediate Similarity	NPC55158
0.6923	Remote Similarity	NPC216129
0.6923	Remote Similarity	NPC130449
0.6923	Remote Similarity	NPC248132
0.6818	Remote Similarity	NPC486104
0.6719	Remote Similarity	NPC486107
0.6622	Remote Similarity	NPC185307
0.6579	Remote Similarity	NPC486097
0.6441	Remote Similarity	NPC166040
0.6316	Remote Similarity	NPC112861
0.625	Remote Similarity	NPC486100
0.625	Remote Similarity	NPC486101
0.6197	Remote Similarity	NPC18979
0.6184	Remote Similarity	NPC470950
0.6133	Remote Similarity	NPC39657
0.6129	Remote Similarity	NPC472024
0.6129	Remote Similarity	NPC270849
0.6104	Remote Similarity	NPC470235
0.6032	Remote Similarity	NPC26653
0.6032	Remote Similarity	NPC80600
0.6	Remote Similarity	NPC302378
0.5938	Remote Similarity	NPC248355
0.589	Remote Similarity	NPC486106
0.5846	Remote Similarity	NPC55040
0.5802	Remote Similarity	NPC11411
0.5769	Remote Similarity	NPC486099
0.5741	Remote Similarity	NPC121783
0.5741	Remote Similarity	NPC34902
0.5741	Remote Similarity	NPC18449
0.5735	Remote Similarity	NPC37468
0.5735	Remote Similarity	NPC604095
0.5696	Remote Similarity	NPC129417
0.5694	Remote Similarity	NPC158635
0.5694	Remote Similarity	NPC229882
0.5692	Remote Similarity	NPC479029
0.5676	Remote Similarity	NPC486109
0.5676	Remote Similarity	NPC486108
0.5636	Remote Similarity	NPC228907
0.56	Remote Similarity	NPC486105
0.5556	Remote Similarity	NPC9912
0.55	Remote Similarity	NPC25817
0.55	Remote Similarity	NPC283995
0.5455	Remote Similarity	NPC217635
0.5385	Remote Similarity	NPC479028
0.5385	Remote Similarity	NPC43508
0.5385	Remote Similarity	NPC479031
0.5345	Remote Similarity	NPC222127
0.5345	Remote Similarity	NPC82862
0.5254	Remote Similarity	NPC606146
0.525	Remote Similarity	NPC486103
0.5238	Remote Similarity	NPC27843
0.5238	Remote Similarity	NPC7171
0.5213	Remote Similarity	NPC475224
0.5185	Remote Similarity	NPC46092
0.5185	Remote Similarity	NPC163635
0.5181	Remote Similarity	NPC269559
0.5161	Remote Similarity	NPC299144
0.5128	Remote Similarity	NPC605526
0.5125	Remote Similarity	NPC299706
0.5125	Remote Similarity	NPC245615
0.5125	Remote Similarity	NPC115466
0.5125	Remote Similarity	NPC61604
0.5082	Remote Similarity	NPC153149
0.5082	Remote Similarity	NPC227160
0.5082	Remote Similarity	NPC82111
0.506	Remote Similarity	NPC476352
0.5057	Remote Similarity	NPC149873

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC205796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4003
0.1-0.2	4966
0.2-0.3	167
0.3-0.4	13
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