NPASS Compound

Natural Product: NPC93350

Natural Product ID	NPC93350
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RIEOGMJFSBPALR-XQRDKSHNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

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 59 62 0 0 0 0 0 0 0 0999 V2000 -2.7739 -0.7617 -3.5977 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -0.2247 -2.2078 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1144 -0.7970 -1.7568 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0833 -1.5102 -0.7320 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0627 -0.5537 -2.4547 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2488 -1.1192 -1.9832 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -2.3641 -2.4164 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7995 -2.9697 -1.9885 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5910 -2.2796 -1.0761 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7538 -2.8707 -0.6340 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0793 -4.0085 -1.0548 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5181 -2.1452 0.2803 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1258 -0.9056 0.7134 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9410 -0.1671 1.6689 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5198 1.0994 2.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2497 1.8410 2.9975 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4288 1.3539 3.5113 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8725 0.1148 3.1143 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1193 -0.6032 2.2107 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1836 2.0871 4.4245 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9943 -0.3686 0.2619 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2540 -1.0256 -0.5981 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0620 -0.4735 -1.0812 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2186 -4.2226 -2.4113 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4180 -0.5993 -1.3608 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1170 0.4664 -0.8014 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9188 0.4999 0.6988 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6660 1.7046 1.2324 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0975 1.5950 0.7807 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0950 1.5841 -0.7327 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4881 1.6258 -1.2628 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9282 0.6927 -1.9703 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2990 2.7009 -0.9716 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4665 0.4322 -1.1393 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9142 2.5622 1.3195 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5788 1.7696 2.6243 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5550 0.6237 0.9627 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2420 -0.2352 -4.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8637 -0.5764 -3.7018 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6451 -1.8653 -3.6296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3199 0.8866 -2.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0110 -2.9003 -3.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4167 -2.6343 0.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6020 1.4951 1.7055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9348 2.8202 3.3351 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8139 -0.2834 3.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4837 -1.5868 1.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7134 2.6147 5.1381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7732 0.5037 -0.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9593 -5.0843 -1.9917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6594 1.3959 -1.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3331 -0.4369 1.1198 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1924 2.6046 0.7769 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4651 0.5797 1.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5308 2.4712 -1.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0180 2.9755 -1.6571 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4286 3.1880 1.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4243 1.3438 2.9651 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3349 -0.0594 1.6425 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 3 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 17 20 1 0 13 21 1 0 21 22 1 0 22 23 2 0 8 24 1 0 2 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 29 35 1 0 28 36 1 0 27 37 1 0 23 6 1 0 34 26 1 0 22 9 1 0 19 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 6 7 42 1 0 12 43 1 0 15 44 1 0 16 45 1 0 18 46 1 0 19 47 1 0 20 48 1 0 23 49 1 0 24 50 1 0 26 51 1 6 27 52 1 1 28 53 1 6 29 54 1 1 30 55 1 6 33 56 1 0 35 57 1 0 36 58 1 0 37 59 1 0 M END

Standard InCHIKey	RIEOGMJFSBPALR-XQRDKSHNSA-N
Standard InCHI	InChI=1S/C24H22O13/c1-9(34-24-20(30)18(28)19(29)21(37-24)22(31)32)23(33)35-12-6-13(26)17-14(27)8-15(36-16(17)7-12)10-2-4-11(25)5-3-10/h2-9,18-21,24-26,28-30H,1H3,(H,31,32)/t9-,18-,19-,20+,21-,24+/m1/s1
SMILES	C[C@H](C(=O)Oc1cc(c2c(=O)cc(c3ccc(cc3)O)oc2c1)O)O[C@@H]1[C@H]([C@@H]([C@H]([C@H](C(=O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.11	Volume:	477.343 ? Van der Waals volume.
Dense:	1.085	LogP:	1.021 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.376 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.518 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	26.0
TPSA:	213.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.189	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.215	Fsp³:	0.292
MCE-18:	93.032 ? 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:	0.44	Fluc inhibitor:	0.331 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.915 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.892 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.2	Promiscuous compounds:	0.372

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.483	MDCK Permeability:	-5.182
Pgp-inhibitor:	0.0	Pgp-substrate:	0.17
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):	0.124
20% Bioavailability (F20%):	0.385	30% Bioavailability (F30%):	0.815
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.858
Plasma Protein Binding (PPB):	81.942%	Volume Distribution (VD):	-0.077
Fu:	14.821% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.195
OATP1B3 inhibitor:	0.947	BCRP inhibitor:	0.015
BSEP inhibitor:	0.06

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.031
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.005 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.199

Half-life (T1/2):

3.194

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.089
Human Hepatotoxicity (H-HT):	0.35	Drug-induced Liver Injury (DILI):	0.983
AMES Toxicity:	0.618	Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.075	Skin Sensitization:	0.958
Carcinogencity:	0.064	Eye Corrosion:	0.0
Eye Irritation:	0.663	Respiratory Toxicity:	0.044
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.507
Hematotoxicity:	0.053	Drug-induced Nephrotoxicity:	0.606
Genotoxicity:	0.972	RPMI-8226 Immunitoxicity:	0.101
A549 Cytotoxicity:	0.027	Hek293 Cytotoxicity:	0.266
BCF:	0.327 ? 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:	2.99 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.393 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.545 ? 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
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14709876]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	twig	n.a.	PMID[14709876]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[15043402]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	stem wood	n.a.	n.a.	PMID[16180806]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309320]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[16792412]
NPO23769	Ainsliaea macrocephala	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18484734]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18489163]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19128011]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	leaves and stems	Kunming, Yunnan, China	2007-AUG	PMID[19133780]
NPO18735	Pinus mugo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31475763]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31983544]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32092043]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36866384]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36929733]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37151483]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38931446]
NPO21352	Boronia ternata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23721	Epidendrum rigidum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24993	Conospermum teretifolium	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23849	Dicoma anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24462	Pityrogramma ebenea	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24952	Galeopsis tetrahit	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23896	Cytisus ratisbonensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18735	Pinus mugo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23302	Strychnos camptoneura	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23302	Strychnos camptoneura	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21478	Buxus hyrcana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25037	Nepeta cataria	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21352	Boronia ternata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23302	Strychnos camptoneura	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24015	Perknaster fuscus	Species	Ganeriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24258	Vellozia nivea	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23769	Ainsliaea macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23849	Dicoma anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24301	Buxus microphylla	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21478	Buxus hyrcana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23896	Cytisus ratisbonensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25080	Sphaeria maculans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18735	Pinus mugo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24952	Galeopsis tetrahit	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23930	Luculia pinceana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24462	Pityrogramma ebenea	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28748	Aphis sambuci	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24993	Conospermum teretifolium	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23428	Tinus mamillata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20498	Cephalaria ambrosioides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23474	Abies veitchii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22684	Enrichment culture	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18918	Lecanicillium muscarium	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23721	Epidendrum rigidum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7197	Colchicum robustum	Species	Colchicaceae	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 NPC93350 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	14594
0.1-0.2	32083
0.2-0.3	2427
0.3-0.4	579
0.4-0.5	138
0.5-0.6	32
0.6-0.7	4
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
0.7381	Intermediate Similarity	NPC282169
0.6591	Remote Similarity	NPC20505
0.6531	Remote Similarity	NPC253685
0.6517	Remote Similarity	NPC608742
0.625	Remote Similarity	NPC64051
0.5978	Remote Similarity	NPC43211
0.5843	Remote Similarity	NPC331652
0.58	Remote Similarity	NPC229409
0.5773	Remote Similarity	NPC44931
0.5761	Remote Similarity	NPC27942
0.5604	Remote Similarity	NPC39360
0.5604	Remote Similarity	NPC29763
0.5604	Remote Similarity	NPC210003
0.5532	Remote Similarity	NPC210094
0.5446	Remote Similarity	NPC46202
0.54	Remote Similarity	NPC65003
0.5361	Remote Similarity	NPC190003
0.5333	Remote Similarity	NPC101636
0.5309	Remote Similarity	NPC234133
0.5288	Remote Similarity	NPC270675
0.5288	Remote Similarity	NPC195685
0.5269	Remote Similarity	NPC19709
0.5248	Remote Similarity	NPC210073
0.5208	Remote Similarity	NPC237435
0.5189	Remote Similarity	NPC298171
0.5155	Remote Similarity	NPC610187
0.5152	Remote Similarity	NPC600989
0.5143	Remote Similarity	NPC479766
0.514	Remote Similarity	NPC472994
0.5098	Remote Similarity	NPC22062
0.5098	Remote Similarity	NPC473634
0.5098	Remote Similarity	NPC138811
0.5094	Remote Similarity	NPC479765
0.5088	Remote Similarity	NPC298666
0.5053	Remote Similarity	NPC189142
0.5053	Remote Similarity	NPC77660
0.5049	Remote Similarity	NPC122809

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC93350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3121
0.1-0.2	5888
0.2-0.3	132
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
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
0.5208	Remote Similarity	NPD4338	Clinical (unspecified phase)

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