NPASS Compound

Natural Product: NPC98213

Natural Product ID	NPC98213
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JFNHZWHKRGPMBT-BSPVHXKKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101242525
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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 61 64 0 0 0 0 0 0 0 0999 V2000 -1.6991 0.5891 -3.4859 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5493 0.4526 -1.9932 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8209 -0.5144 -1.5106 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6717 -0.6500 -0.0392 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4056 -2.1008 0.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7620 -2.7853 0.2822 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0098 -3.4234 1.6228 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9096 -3.8476 -0.7728 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7420 -1.6823 0.1194 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8755 -1.8397 -0.2974 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0384 -0.4573 0.5579 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7088 0.8136 0.1716 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5316 1.8183 1.2890 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2293 1.4048 -1.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8309 2.8659 -1.0779 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0789 2.4546 -1.7893 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0767 0.5711 0.0595 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1788 0.2310 0.5355 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4882 0.2235 0.1238 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9994 1.4838 -0.4307 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3414 1.9384 -0.0334 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9643 1.2041 1.1225 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5875 -0.2646 0.9722 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2632 -1.0148 2.0834 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6475 -0.9662 1.8346 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2215 -0.2968 1.1924 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3198 1.3986 1.2003 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3653 3.2958 0.2955 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9491 1.4332 -1.8459 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2614 1.5299 -3.8294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7513 0.4438 -3.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1293 -0.2326 -4.0025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3171 -1.2293 -2.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1391 -2.5607 -0.6227 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0910 -2.3047 1.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8780 -4.1253 1.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3516 -2.6887 2.3870 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1549 -4.0343 1.9701 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6427 -4.6057 -0.3955 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9611 -4.3878 -0.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3443 -3.4540 -1.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9121 -0.5117 1.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4850 2.1424 1.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7976 1.3056 2.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2389 2.6679 1.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9709 3.1852 -1.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9388 3.4453 -0.1584 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0741 2.4938 -2.9115 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0196 2.7819 -1.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4414 0.7661 -0.8292 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5703 -0.5811 -0.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2646 2.3046 -0.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0720 1.8354 -0.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5166 1.5322 2.0861 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8932 -0.6700 -0.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9719 -2.0834 2.1235 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0619 -0.4828 3.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8424 -1.2358 0.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6426 2.0680 0.5215 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0051 3.8204 -0.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2138 0.5301 -2.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 6 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 12 17 1 6 4 18 1 1 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 22 27 1 0 21 28 1 0 20 29 1 0 14 2 1 0 26 19 1 0 11 4 1 0 16 14 1 0 1 30 1 0 1 31 1 0 1 32 1 0 3 33 1 0 5 34 1 0 5 35 1 0 7 36 1 0 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 8 41 1 0 11 42 1 1 13 43 1 0 13 44 1 0 13 45 1 0 15 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 17 50 1 0 19 51 1 6 20 52 1 1 21 53 1 6 22 54 1 1 23 55 1 6 24 56 1 0 24 57 1 0 25 58 1 0 27 59 1 0 28 60 1 0 29 61 1 0 M END

Standard InCHIKey	JFNHZWHKRGPMBT-BSPVHXKKSA-N
Standard InCHI	InChI=1S/C21H32O8/c1-10-7-21(29-17-14(25)13(24)12(23)11(8-22)28-17)9-18(2,3)16(26)15(21)19(4,27)20(10)5-6-20/h7,11-15,17,22-25,27H,5-6,8-9H2,1-4H3/t11-,12-,13+,14-,15-,17+,19+,21+/m1/s1
SMILES	CC1=C[C@@]2(CC(C)(C)C(=O)[C@@H]2[C@@](C)(C21CC2)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.21	Volume:	402.595 ? Van der Waals volume.
Dense:	1.024	LogP:	0.6 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.3 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.194 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	20.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.397	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.588	Fsp³:	0.857
MCE-18:	117.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.41	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.027 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.164	Promiscuous compounds:	0.339

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.705	MDCK Permeability:	-5.124
Pgp-inhibitor:	0.002	Pgp-substrate:	0.04
PAMPA:	0.995 ? 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):	0.507
20% Bioavailability (F20%):	0.113	30% Bioavailability (F30%):	0.585
50% Bioavailability (F50%):	0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.842
Plasma Protein Binding (PPB):	68.172%	Volume Distribution (VD):	-0.278
Fu:	30.702% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.198

ADMET: Metabolism

CYP1A2-inhibitor:	0.018	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.031	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.144
HLM stability:	0.514 ? 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):

2.721

Half-life (T1/2):

2.2

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.062
Human Hepatotoxicity (H-HT):	0.665	Drug-induced Liver Injury (DILI):	0.635
AMES Toxicity:	0.897	Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.042	Skin Sensitization:	0.997
Carcinogencity:	0.504	Eye Corrosion:	0.0
Eye Irritation:	0.293	Respiratory Toxicity:	0.069
Drug-induced Neurotoxicity:	0.124	Ototoxicity:	0.921
Hematotoxicity:	0.616	Drug-induced Nephrotoxicity:	0.804
Genotoxicity:	0.887	RPMI-8226 Immunitoxicity:	0.174
A549 Cytotoxicity:	0.339	Hek293 Cytotoxicity:	0.351
BCF:	0.618 ? 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:	3.072 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.527 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.658 ? 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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	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 NPC98213 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	15935
0.1-0.2	28251
0.2-0.3	4983
0.3-0.4	650
0.4-0.5	40
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC98213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6400
0.1-0.2	2606
0.2-0.3	122
0.3-0.4	22
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