NPASS Compound

Natural Product: NPC63988

Natural Product ID	NPC63988
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DPKLBEWKXLCUQW-UQQDFEJISA-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:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 84 89 0 0 0 0 0 0 0 0999 V2000 -5.8387 -1.7558 1.1981 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3563 -1.1510 -0.0756 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4335 -0.1353 0.2441 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8678 1.2163 -0.0669 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4110 1.2030 0.4274 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6422 0.3562 -0.5085 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3965 -0.7087 -0.9330 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4340 -0.1073 -0.0748 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3327 0.2452 -0.7862 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4900 1.1538 0.0816 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5712 0.3980 0.9756 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2175 -0.6922 0.3101 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2171 -1.9875 0.9490 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0469 -2.0394 1.8245 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6805 -0.5480 0.5915 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3170 -1.8563 1.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7199 -1.5330 1.4956 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5583 -0.9041 0.4028 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8746 -1.9426 -0.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7456 -0.2523 1.0513 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0940 0.9990 1.6347 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0052 1.4135 0.6864 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8647 0.2720 -0.2549 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4794 -0.1164 -0.5981 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7027 0.9139 -1.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5579 0.1780 -2.0337 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0920 -0.8362 -1.1586 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5684 -0.9000 -1.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4221 -2.1051 -1.5274 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5551 0.5497 -1.4329 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8343 0.1283 0.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1491 1.3868 -0.1857 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2605 1.4416 -1.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8003 2.4859 -1.6115 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6011 0.1367 -1.3642 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7836 -0.7366 -0.6152 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0476 2.5659 0.3731 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5746 2.2645 0.4609 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9859 3.0929 -0.5934 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5605 -0.3056 -0.5852 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5532 -1.5382 2.0188 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8522 -1.4223 1.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7924 -2.8787 1.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8978 -1.9869 -0.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7710 -0.2072 1.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7974 1.2839 -1.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3617 0.9223 1.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4353 0.9767 -1.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6820 0.8927 -1.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9937 1.9530 -0.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2065 1.7121 0.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1808 0.0263 1.8433 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1482 1.1238 1.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2212 -2.9231 0.6234 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7780 0.1424 1.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7552 -2.1022 2.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2202 -2.6623 0.3452 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2198 -2.5022 1.7327 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6791 -0.9726 2.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9383 -2.5655 -0.7211 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0234 -1.5150 -1.6175 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6354 -2.6457 -0.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1104 -0.9310 1.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6044 0.7737 2.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8199 1.7906 1.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2990 2.3208 0.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0682 1.6910 1.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5499 -1.0199 -1.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3831 1.7684 -0.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 1.3051 -2.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0277 -0.3115 -2.9392 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1747 0.9041 -2.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7324 -0.9736 -2.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9328 -1.8291 -0.8543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5829 -2.0857 -2.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1087 0.2058 -2.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6833 2.3204 0.1726 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3315 -1.4427 -1.3189 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4123 -1.2889 0.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7308 3.1366 0.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1213 3.4918 -1.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5984 3.9425 -0.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6243 2.5439 -1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9084 -1.2118 -0.5685 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 2 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 6 23 30 1 6 20 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 5 37 1 0 4 38 1 0 38 39 1 0 3 40 1 0 7 2 1 0 28 9 1 0 36 31 1 0 27 12 1 0 24 15 1 0 23 18 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 6 3 45 1 1 4 46 1 6 5 47 1 1 6 48 1 6 9 49 1 6 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 15 55 1 1 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 1 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 24 68 1 6 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 32 77 1 0 36 78 1 0 36 79 1 0 37 80 1 0 39 81 1 0 39 82 1 0 39 83 1 0 40 84 1 0 M END

Standard InCHIKey	DPKLBEWKXLCUQW-UQQDFEJISA-N
Standard InCHI	InChI=1S/C30H44O10/c1-16-23(33)25(37-3)24(34)26(39-16)40-18-4-9-28(15-31)20-5-8-27(2)19(17-12-22(32)38-14-17)7-11-30(27,36)21(20)6-10-29(28,35)13-18/h12,15-16,18-21,23-26,33-36H,4-11,13-14H2,1-3H3/t16-,18-,19+,20-,21+,23-,24-,25+,26+,27+,28-,29-,30-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)O[C@H]1CC[C@]2(C=O)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)C1=CC(=O)OC1)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	564.29	Volume:	556.09 ? Van der Waals volume.
Dense:	1.015	LogP:	0.673 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.415 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.858 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	151.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.219	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.37	Fsp³:	0.867
MCE-18:	115.679 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.788	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.161	Promiscuous compounds:	0.563

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.076	MDCK Permeability:	-5.263
Pgp-inhibitor:	0.003	Pgp-substrate:	0.992
PAMPA:	0.991 ? 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):	0.056
20% Bioavailability (F20%):	0.529	30% Bioavailability (F30%):	0.642
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.157	MRP1:	0.445
Plasma Protein Binding (PPB):	55.551%	Volume Distribution (VD):	-0.263
Fu:	49.181% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.041
BSEP inhibitor:	0.8

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.117
HLM stability:	0.056 ? 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):

1.607

Half-life (T1/2):

4.084

ADMET: Toxicity

hERG Blockers:	0.138	hERG Blockers (10um):	0.68
Human Hepatotoxicity (H-HT):	0.847	Drug-induced Liver Injury (DILI):	0.693
AMES Toxicity:	0.761	Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.939	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.964
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.673
Hematotoxicity:	0.325	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.842
A549 Cytotoxicity:	0.45	Hek293 Cytotoxicity:	0.978
BCF:	0.543 ? 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:	3.302 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.934 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.159 ? 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
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np020518b]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762814]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679307]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	Australian rainforest	n.a.	PMID[18039010]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20218657]
NPO17202	Lasallia asiae-orientalis	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25866	Kaunia lasiophthalma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9565	Linum maritimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7535	Mansonia altissima	Species	Culicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11354	Streptomyces galbus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13058	Psychotria brachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2124	Bulgaria inquinans	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10273	Dictyota flabellata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2124	Bulgaria inquinans	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9794	Dysoxylum fraseranum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13058	Psychotria brachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24924	Saara hardwickii	Species	Agamidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17202	Lasallia asiae-orientalis	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3546	Shorea balangeran	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25866	Kaunia lasiophthalma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8878	Polygala arenaria	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6423	Vitex cauliflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11158	Diplopterygium rufopilosum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7535	Mansonia altissima	Species	Culicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6878	Vesperus xatarti	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11510	Astragalus flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12123	Geodia gigas	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4348	Watasenia scintillans	Species	Enoploteuthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9565	Linum maritimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11354	Streptomyces galbus	Species	Streptomycetaceae	Bacteria	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 NPC63988 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	14446
0.1-0.2	31527
0.2-0.3	3591
0.3-0.4	94
0.4-0.5	93
0.5-0.6	52
0.6-0.7	36
0.7-0.8	2
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
0.8095	Intermediate Similarity	NPC469749
0.7949	Intermediate Similarity	NPC6108
0.7949	Intermediate Similarity	NPC89514
0.775	Intermediate Similarity	NPC250556
0.775	Intermediate Similarity	NPC180079
0.7722	Intermediate Similarity	NPC17896
0.7722	Intermediate Similarity	NPC469755
0.7722	Intermediate Similarity	NPC284406
0.7722	Intermediate Similarity	NPC197707
0.7722	Intermediate Similarity	NPC251866
0.7407	Intermediate Similarity	NPC199428
0.7407	Intermediate Similarity	NPC109448
0.7407	Intermediate Similarity	NPC10823
0.7407	Intermediate Similarity	NPC310341
0.7375	Intermediate Similarity	NPC219085
0.7229	Intermediate Similarity	NPC305574
0.7073	Intermediate Similarity	NPC486126
0.6951	Remote Similarity	NPC486129
0.6882	Remote Similarity	NPC329636
0.6667	Remote Similarity	NPC34390
0.663	Remote Similarity	NPC146857
0.663	Remote Similarity	NPC247190
0.6627	Remote Similarity	NPC99728
0.6627	Remote Similarity	NPC87250
0.6627	Remote Similarity	NPC244402
0.6627	Remote Similarity	NPC50305
0.6556	Remote Similarity	NPC32793
0.6556	Remote Similarity	NPC116075
0.6471	Remote Similarity	NPC157376
0.6471	Remote Similarity	NPC142066
0.6471	Remote Similarity	NPC603972
0.6413	Remote Similarity	NPC55532
0.6374	Remote Similarity	NPC608063
0.6327	Remote Similarity	NPC194716
0.631	Remote Similarity	NPC158344
0.625	Remote Similarity	NPC9499
0.625	Remote Similarity	NPC471360
0.625	Remote Similarity	NPC469751
0.625	Remote Similarity	NPC471361
0.625	Remote Similarity	NPC86159
0.625	Remote Similarity	NPC469752
0.625	Remote Similarity	NPC469754
0.625	Remote Similarity	NPC70542
0.6196	Remote Similarity	NPC486151
0.6163	Remote Similarity	NPC84987
0.6162	Remote Similarity	NPC329675
0.6154	Remote Similarity	NPC72772
0.6129	Remote Similarity	NPC475629
0.6118	Remote Similarity	NPC474418
0.6092	Remote Similarity	NPC479356
0.6092	Remote Similarity	NPC479355
0.6067	Remote Similarity	NPC471359
0.6	Remote Similarity	NPC469753
0.5955	Remote Similarity	NPC484212
0.5909	Remote Similarity	NPC469750
0.5889	Remote Similarity	NPC93883
0.587	Remote Similarity	NPC5883
0.5795	Remote Similarity	NPC309034
0.5682	Remote Similarity	NPC99620
0.5667	Remote Similarity	NPC84949
0.5667	Remote Similarity	NPC480562
0.5667	Remote Similarity	NPC74945
0.5667	Remote Similarity	NPC31354
0.5667	Remote Similarity	NPC69576
0.5604	Remote Similarity	NPC77319
0.5604	Remote Similarity	NPC471351
0.5604	Remote Similarity	NPC471355
0.5567	Remote Similarity	NPC59288
0.5543	Remote Similarity	NPC483822
0.5521	Remote Similarity	NPC480910
0.5521	Remote Similarity	NPC480909
0.551	Remote Similarity	NPC232785
0.551	Remote Similarity	NPC486139
0.5495	Remote Similarity	NPC76572
0.5495	Remote Similarity	NPC193382
0.5495	Remote Similarity	NPC480914
0.5444	Remote Similarity	NPC484211
0.5375	Remote Similarity	NPC97487
0.5361	Remote Similarity	NPC475556
0.5361	Remote Similarity	NPC311706
0.5333	Remote Similarity	NPC479351
0.5333	Remote Similarity	NPC479352
0.5319	Remote Similarity	NPC471354
0.5319	Remote Similarity	NPC27507
0.5269	Remote Similarity	NPC88668
0.5253	Remote Similarity	NPC486143
0.5253	Remote Similarity	NPC486135
0.5253	Remote Similarity	NPC486142
0.5253	Remote Similarity	NPC486137
0.5253	Remote Similarity	NPC486149
0.5244	Remote Similarity	NPC10232
0.5217	Remote Similarity	NPC5311
0.5217	Remote Similarity	NPC77299
0.5217	Remote Similarity	NPC480906
0.5217	Remote Similarity	NPC480915
0.5213	Remote Similarity	NPC484202
0.5165	Remote Similarity	NPC471633
0.5149	Remote Similarity	NPC329986
0.5149	Remote Similarity	NPC140092
0.5109	Remote Similarity	NPC196429
0.5109	Remote Similarity	NPC203862
0.5098	Remote Similarity	NPC486138
0.5098	Remote Similarity	NPC276838
0.5051	Remote Similarity	NPC188234
0.5051	Remote Similarity	NPC240070

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC63988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5880
0.1-0.2	3145
0.2-0.3	111
0.3-0.4	1
0.4-0.5	10
0.5-0.6	1
0.6-0.7	0
0.7-0.8	2
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
0.775	Intermediate Similarity	NPD7507	Pre-clinical
0.7722	Intermediate Similarity	NPD7319	Approved
0.5376	Remote Similarity	NPD7516	Pre-clinical

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