NPASS Compound

Natural Product: NPC43508

Natural Product ID	NPC43508
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-Dehydrodiconiferyl Alcohol 4-O-Beta-D-Glucopyranoside
IUPAC Name	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(2S,3R)-3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1086907
PubChem CID	5316442
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 10.5413 0.1150 1.4776 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7575 0.5053 0.4047 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4468 -0.2358 0.4043 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3030 0.4104 0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9891 -0.2120 0.4914 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7798 -1.5515 0.4155 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5053 -2.0961 0.4262 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3196 -3.4649 0.3477 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4623 -4.2918 0.2565 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4037 -1.2465 0.5174 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5879 0.1205 0.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8620 0.5970 0.5810 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2669 0.8170 0.6862 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2506 1.8037 1.8186 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2199 2.7882 1.6810 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3387 -0.3351 1.0471 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0341 -1.4733 0.5511 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0022 -0.1838 0.4754 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0548 0.1141 1.3144 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3666 0.2747 0.8521 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6293 0.1326 -0.4871 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5745 -0.1701 -1.3579 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2992 -0.3191 -0.8578 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8502 -0.3123 -2.7142 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8829 -0.6119 -3.6730 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8793 0.2740 -1.0102 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0726 0.5689 -0.3638 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9907 -0.4339 -0.6621 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1574 -0.3189 0.0824 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2456 -1.0401 -0.6900 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8718 -2.3836 -0.8409 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5870 1.0913 0.3026 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0612 2.0125 -0.7854 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5806 1.8954 -0.9428 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9195 2.8985 -0.2331 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6775 1.6467 -2.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2365 1.5769 1.5608 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0658 -0.6868 1.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2803 0.2016 -0.5250 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5687 1.5939 0.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4443 -1.3027 0.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3771 1.4969 0.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6515 -2.2120 0.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1209 -3.9476 -0.5864 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1929 -5.3633 0.1452 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0986 -4.2173 1.1716 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0032 1.6784 0.6432 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0178 1.2499 -0.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3719 1.2236 2.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2718 2.2845 1.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5683 2.9871 2.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2795 -0.4730 2.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8678 0.2314 2.3826 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1650 0.5117 1.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5457 -0.5559 -1.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1903 -1.3839 -3.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2619 0.2295 -3.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3147 -1.1285 -4.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9863 0.7061 0.7184 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0078 -0.7997 1.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4102 -0.5887 -1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2099 -1.0614 -0.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3374 -2.6607 -0.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6942 1.1366 0.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3912 3.0447 -0.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2451 1.9620 -1.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9479 3.7652 -0.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0510 1.1657 -2.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9066 0.8712 2.1581 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 2 0 6 7 1 0 7 8 1 0 8 9 1 0 7 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 13 16 1 0 16 17 1 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 12 5 1 0 23 18 1 0 34 27 1 0 17 10 1 0 1 38 1 0 2 39 1 0 2 40 1 0 3 41 1 0 4 42 1 0 6 43 1 0 9 44 1 0 9 45 1 0 9 46 1 0 12 47 1 0 13 48 1 6 14 49 1 0 14 50 1 0 15 51 1 0 16 52 1 1 19 53 1 0 20 54 1 0 23 55 1 0 25 56 1 0 25 57 1 0 25 58 1 0 27 59 1 1 29 60 1 1 30 61 1 0 30 62 1 0 31 63 1 0 32 64 1 1 33 65 1 1 34 66 1 6 35 67 1 0 36 68 1 0 37 69 1 0 M END

Standard InCHIKey	SPWHQAUMLDQOFU-QXGRHDLQSA-N
Standard InCHI	InChI=1S/C26H32O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h3-6,8-10,16,20-24,26-32H,7,11-12H2,1-2H3/b4-3+/t16-,20+,21+,22-,23+,24+,26+/m0/s1
SMILES	OC/C=C/c1cc(OC)c2c(c1)[C@H](CO)[C@H](O2)c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	520.19	Volume:	502.264 ? Van der Waals volume.
Dense:	1.036	LogP:	1.052 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.588 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.59 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	167.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.265	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.371	Fsp³:	0.462
MCE-18:	87.579 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.587	Fluc inhibitor:	0.393 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.085 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.512 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.191	Promiscuous compounds:	0.08

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.465	MDCK Permeability:	-5.058
Pgp-inhibitor:	0.003	Pgp-substrate:	0.075
PAMPA:	0.606 ? 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):	0.527
20% Bioavailability (F20%):	0.227	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.013
Plasma Protein Binding (PPB):	75.924%	Volume Distribution (VD):	-0.258
Fu:	21.507% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.496
BSEP inhibitor:	0.169

ADMET: Metabolism

CYP1A2-inhibitor:	0.224	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.221	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.013
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.05
HLM stability:	0.019 ? 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):

2.426

Half-life (T1/2):

3.634

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.049
Human Hepatotoxicity (H-HT):	0.931	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.926	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.05	Skin Sensitization:	0.998
Carcinogencity:	0.27	Eye Corrosion:	0.0
Eye Irritation:	0.106	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.975
Hematotoxicity:	0.528	Drug-induced Nephrotoxicity:	0.777
Genotoxicity:	0.629	RPMI-8226 Immunitoxicity:	0.141
A549 Cytotoxicity:	0.448	Hek293 Cytotoxicity:	0.229
BCF:	0.562 ? 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:	3.117 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.944 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.862 ? 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
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO14524	Delisea pulchra	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933872]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19467876]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	aerial parts	Khon Kaen Province, Thailand	2006-Aug	PMID[19943620]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO27759	Fusarium poae	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37371939]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37569477]
NPO27022	Neisseria meningitidis	Species	Neisseriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4990768]
NPO27523	Brickellia glutinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6436442]
NPO14017	Bulbine abyssinica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29171	Ascochyta salicorniae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27523	Brickellia glutinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27759	Fusarium poae	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8618	Hypotrachyna cirrhata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27022	Neisseria meningitidis	Species	Neisseriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27536	Sidastrum quinquenervium	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27177	Telitoxicum glaziovii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5546	Calycophyllum spruceanum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14524	Delisea pulchra	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12937	Tithonia pedunculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5546	Calycophyllum spruceanum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30113	Cistanche tubelosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14524	Delisea pulchra	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27536	Sidastrum quinquenervium	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8618	Hypotrachyna cirrhata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27177	Telitoxicum glaziovii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11394	Dichroa febrifuga	Species	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29171	Ascochyta salicorniae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27523	Brickellia glutinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27759	Fusarium poae	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5546	Calycophyllum spruceanum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21864	Agathis alba	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5051	Lobelia urens	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27022	Neisseria meningitidis	Species	Neisseriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3224	Chloridium virescens	Species	Chaetosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13240	Pinguipes brasilianus	Species	Pinguipedidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8396	Quercus macrocarpa	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9459	Piper hoffmannseggianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14017	Bulbine abyssinica	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27416	Ceratonia siliqua	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12937	Tithonia pedunculata	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
Activity	6

Activity Type	# Activity
Cell line	6

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
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	0.3	uM	PMID[19943620]
NPT83	Cell line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[19943620]
NPT396	Cell line	T47D	Homo sapiens	Activity	<	0.1	uM	PMID[19943620]
NPT396	Cell line	T47D	Homo sapiens	Activity	=	63.0	uM	PMID[19943620]
NPT396	Cell line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[19943620]

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 NPC43508 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	18044
0.1-0.2	28231
0.2-0.3	2823
0.3-0.4	597
0.4-0.5	115
0.5-0.6	33
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC269559
0.7273	Intermediate Similarity	NPC217635
0.7059	Intermediate Similarity	NPC26394
0.6812	Remote Similarity	NPC248355
0.6707	Remote Similarity	NPC479448
0.65	Remote Similarity	NPC476301
0.6296	Remote Similarity	NPC270751
0.622	Remote Similarity	NPC79429
0.5854	Remote Similarity	NPC199539
0.5811	Remote Similarity	NPC55040
0.5733	Remote Similarity	NPC302378
0.5733	Remote Similarity	NPC156502
0.5733	Remote Similarity	NPC10737
0.5694	Remote Similarity	NPC49074
0.5541	Remote Similarity	NPC87725
0.5541	Remote Similarity	NPC263261
0.5385	Remote Similarity	NPC276753
0.5385	Remote Similarity	NPC205796
0.5316	Remote Similarity	NPC37468
0.5316	Remote Similarity	NPC246947
0.5253	Remote Similarity	NPC316539
0.5227	Remote Similarity	NPC478701
0.5227	Remote Similarity	NPC260397
0.5205	Remote Similarity	NPC166040
0.52	Remote Similarity	NPC270849
0.5195	Remote Similarity	NPC104167
0.5165	Remote Similarity	NPC302610
0.5125	Remote Similarity	NPC604095
0.5065	Remote Similarity	NPC479029
0.5062	Remote Similarity	NPC253878
0.5062	Remote Similarity	NPC206413
0.5062	Remote Similarity	NPC482649
0.5062	Remote Similarity	NPC149003
0.5062	Remote Similarity	NPC482647
0.5062	Remote Similarity	NPC482648
0.5062	Remote Similarity	NPC482651
0.5062	Remote Similarity	NPC194244
0.5062	Remote Similarity	NPC482650
0.5059	Remote Similarity	NPC286235
0.5056	Remote Similarity	NPC471667
0.5055	Remote Similarity	NPC275284

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC43508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4557
0.1-0.2	4502
0.2-0.3	81
0.3-0.4	10
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