NPASS Compound

Natural Product: NPC282508

Natural Product ID	NPC282508
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	8-(4-Hydroxy-Benzyl)-7-Methoxy-9,10-Dihydro-Phenanthrene-2,5-Diol
IUPAC Name	8-[(4-hydroxyphenyl)methyl]-7-methoxy-9,10-dihydrophenanthrene-2,5-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL365485
PubChem CID	44392570
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

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 46 49 0 0 0 0 0 0 0 0999 V2000 1.9428 3.7161 -1.2930 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8582 2.6403 -0.3931 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6854 1.9216 -0.2395 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3870 2.3020 -0.9988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6073 1.6148 -0.8927 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6518 2.0523 -1.6918 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6809 0.5634 -0.0106 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5940 0.1737 0.7671 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6161 0.8751 0.6410 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7671 0.4811 1.4592 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8636 -0.1947 0.7182 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8416 -1.5107 0.3150 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9036 -2.1166 -0.3707 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0332 -1.3952 -0.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0783 -0.0744 -0.2771 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0308 0.5143 0.3967 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1183 -1.9141 -1.3405 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6985 -0.8748 1.7779 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8048 -1.8405 1.5831 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9587 -1.3111 0.8407 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9479 -0.2057 0.0182 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0568 0.1855 -0.6776 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2196 -0.5818 -0.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2624 -1.6900 0.2902 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1281 -2.0495 0.9707 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4335 -2.4481 0.4342 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1703 4.5010 -1.0864 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9148 4.2124 -1.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7304 3.3899 -2.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3558 3.1259 -1.7000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6766 2.9988 -2.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5057 -0.0429 2.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2088 1.4529 1.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9774 -2.0971 0.5312 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8404 -3.1555 -0.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9652 0.5141 -0.5062 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0699 1.5602 0.7164 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3345 -2.9086 -1.3799 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2262 -1.4824 1.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8020 -0.3311 2.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1559 -2.2702 2.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4042 -2.7036 0.9816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1327 1.0154 -1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1109 -0.2829 -1.0729 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1941 -2.9234 1.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4191 -3.4065 0.1150 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 5 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 14 17 1 0 8 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 9 3 1 0 16 11 1 0 25 20 1 0 21 7 1 0 1 27 1 0 1 28 1 0 1 29 1 0 4 30 1 0 6 31 1 0 10 32 1 0 10 33 1 0 12 34 1 0 13 35 1 0 15 36 1 0 16 37 1 0 17 38 1 0 18 39 1 0 18 40 1 0 19 41 1 0 19 42 1 0 22 43 1 0 23 44 1 0 25 45 1 0 26 46 1 0 M END

Standard InCHIKey	MXOFIBMBNJWOFF-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C22H20O4/c1-26-21-12-20(25)22-17-9-7-16(24)11-14(17)4-8-18(22)19(21)10-13-2-5-15(23)6-3-13/h2-3,5-7,9,11-12,23-25H,4,8,10H2,1H3
SMILES	COc1cc(O)c2c(c1Cc1ccc(cc1)O)CCc1c2ccc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	348.14	Volume:	366.275 ? Van der Waals volume.
Dense:	0.95	LogP:	3.676 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.238 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.256 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	22.0
TPSA:	69.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.664	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.464	Fsp³:	0.182
MCE-18:	47.385 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.981	Fluc inhibitor:	0.26 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.779 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.388 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.293	Promiscuous compounds:	0.087

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89	MDCK Permeability:	-4.791
Pgp-inhibitor:	0.008	Pgp-substrate:	0.309
PAMPA:	0.587 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.647	30% Bioavailability (F30%):	0.637
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.94
Plasma Protein Binding (PPB):	95.264%	Volume Distribution (VD):	0.604
Fu:	5.991% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.971
OATP1B3 inhibitor:	0.974	BCRP inhibitor:	0.065
BSEP inhibitor:	0.958

ADMET: Metabolism

CYP1A2-inhibitor:	0.994	CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.88	CYP2C19-substrate:	0.696
CYP2C9-inhibitor:	0.928	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.997	CYP2D6-substrate:	0.985
CYP3A4-inhibitor:	0.486	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.007	CYP2C8-inhibitor:	0.995
HLM stability:	0.926 ? 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):

9.227

Half-life (T1/2):

1.318

ADMET: Toxicity

hERG Blockers:	0.299	hERG Blockers (10um):	0.779
Human Hepatotoxicity (H-HT):	0.613	Drug-induced Liver Injury (DILI):	0.127
AMES Toxicity:	0.68	Rat Oral Acute Toxicity:	0.46
Maximum Recommended Daily Dose:	0.879	Skin Sensitization:	0.943
Carcinogencity:	0.703	Eye Corrosion:	0.001
Eye Irritation:	0.852	Respiratory Toxicity:	0.947
Drug-induced Neurotoxicity:	0.532	Ototoxicity:	0.509
Hematotoxicity:	0.168	Drug-induced Nephrotoxicity:	0.176
Genotoxicity:	0.847	RPMI-8226 Immunitoxicity:	0.058
A549 Cytotoxicity:	0.626	Hek293 Cytotoxicity:	0.864
BCF:	1.606 ? 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:	4.879 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.436 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.186 ? 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
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425112]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15686910]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23627123]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	Fibrous Roots	n.a.	n.a.	PMID[25760525]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31415170]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770801]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985392]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836118]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39684253]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39699537]
NPO11893	Telesto riisei	Species	Telestidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7857405]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26125	Pseudomonas corrugata	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13086	Streptomyces carzinostaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO445	Desmarestia aculeata	Species	Desmarestiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14620	Sedum alfredi	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14620	Sedum alfredi	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15591	Tolpis webbii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13319	Isodon lungshengensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8734	Centaurea pabotii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8787	Ariocarpus scapharostrus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11893	Telesto riisei	Species	Telestidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26125	Pseudomonas corrugata	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13086	Streptomyces carzinostaticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12597	Eria barbata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3644	Climacoptera lanata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13913	Ravensara aromatica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6224	Grindelia boliviana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13511	Monopteryx inpae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO445	Desmarestia aculeata	Species	Desmarestiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12919	Clibadium glabrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16226	Prinsepia utilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14509	Stevia seleriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17553	Pleione bulbocodioides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10780	Bletilla striata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7186	Hypogymnia enteromorpha	Species	Parmeliaceae	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	4

Activity Type	# Activity
Individual protein	1
Cell line	1
No target	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2698	Individual protein	Beta tubulin	Leishmania donovani	IC50	=	300000.0	nM	PMID[15686910]

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	=	12000.0	nM	PMID[31415170]
NPT28833	No target	No relevant target	n.a.	IC50	=	12.2	ug.mL-1	PMID[29280630]

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 NPC282508 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	27860
0.1-0.2	18595
0.2-0.3	3257
0.3-0.4	112
0.4-0.5	24
0.5-0.6	7
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6066	Remote Similarity	NPC105620
0.5902	Remote Similarity	NPC37410
0.5833	Remote Similarity	NPC36269
0.5818	Remote Similarity	NPC138248
0.5797	Remote Similarity	NPC478413
0.5517	Remote Similarity	NPC294436
0.5517	Remote Similarity	NPC258780
0.5161	Remote Similarity	NPC113495

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC282508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5450
0.1-0.2	3587
0.2-0.3	112
0.3-0.4	1
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