NPASS Compound

Natural Product: NPC248944

Natural Product ID	NPC248944
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sarsasapogenin
IUPAC Name	n.a.
Synonyms	Sarsasapogenin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1171146
PubChem CID	92095
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 74 79 0 0 0 0 0 0 0 0999 V2000 6.4694 2.1618 -0.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3925 0.7005 -0.7914 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2260 -0.2221 0.3730 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0403 -1.1603 0.2201 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8354 -0.4294 -0.2169 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0606 0.7262 -0.9276 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1876 0.6063 -1.7363 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9528 -1.2155 -0.9936 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9160 -0.3062 -1.1833 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6808 0.3548 0.1601 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8977 -0.0626 0.9402 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4396 1.0986 1.7383 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4137 -0.3065 0.6488 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3590 -0.2885 -0.6801 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6078 -1.0132 -1.5398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7060 -0.8713 -0.5439 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4316 -0.7683 -1.8506 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7878 -1.4384 -1.6562 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5933 -0.6069 -0.6862 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8831 -0.3346 0.5921 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4470 0.0147 0.4689 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7255 -0.1701 1.7862 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3515 0.4986 1.6366 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9725 -1.6121 1.4397 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5853 0.7399 1.3694 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7882 2.0016 0.5446 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7915 1.5980 -0.5448 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0905 0.5996 -1.4055 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9093 1.1063 0.1013 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6670 -1.7010 1.1146 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2124 2.7287 -0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7208 2.2552 0.6991 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4932 2.6867 -0.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2975 0.5098 -1.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1264 0.3417 1.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1619 -0.8120 0.4800 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3599 -1.9831 -0.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8590 -1.6090 1.2201 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1792 1.4603 -2.4360 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1854 -0.3747 -2.2273 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2110 0.4153 -1.9672 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5530 1.4374 0.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7364 -0.8927 1.6258 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0960 0.7120 2.5632 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9462 1.7856 1.0617 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5558 1.6181 2.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4377 0.7504 -1.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4189 -0.9202 -2.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6885 -2.0941 -1.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7299 -1.9276 -0.2285 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5057 0.2445 -2.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9039 -1.4026 -2.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3447 -1.4148 -2.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6284 -2.4601 -1.3070 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4999 -1.2325 -0.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2455 1.0559 0.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5873 -1.2667 1.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2654 0.2144 2.6481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1662 0.4145 2.6276 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4917 1.5281 1.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0048 -2.0033 1.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7669 -1.3312 2.4884 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2409 -2.3536 1.0739 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5956 0.3490 1.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0978 1.0357 2.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1957 2.7850 1.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8631 2.2935 0.0199 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0500 2.4700 -1.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8445 0.2406 -2.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3242 1.1345 -1.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9655 0.1307 0.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5368 -2.1811 0.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1738 -2.3932 1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8934 -1.6443 2.2153 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 6 6 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 20 24 1 1 20 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 13 30 1 1 7 2 1 0 15 9 1 0 21 16 1 0 11 5 1 0 23 13 1 0 28 19 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 6 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 7 39 1 0 7 40 1 0 9 41 1 6 10 42 1 6 11 43 1 1 12 44 1 0 12 45 1 0 12 46 1 0 14 47 1 6 15 48 1 0 15 49 1 0 16 50 1 1 17 51 1 0 17 52 1 0 18 53 1 0 18 54 1 0 19 55 1 1 21 56 1 6 22 57 1 0 22 58 1 0 23 59 1 0 23 60 1 0 24 61 1 0 24 62 1 0 24 63 1 0 25 64 1 0 25 65 1 0 26 66 1 0 26 67 1 0 27 68 1 6 28 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 M END

Standard InCHIKey	GMBQZIIUCVWOCD-WWASVFFGSA-N
Standard InCHI	InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18+,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1
SMILES	C[C@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC[C@H]3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.33	Volume:	450.58 ? Van der Waals volume.
Dense:	0.924	LogP:	5.491 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.47 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.957 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	30.0
TPSA:	38.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.543	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.22	Fsp³:	1.0
MCE-18:	138.667 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.705	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.255	Promiscuous compounds:	0.507

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.132	MDCK Permeability:	-4.955
Pgp-inhibitor:	0.918	Pgp-substrate:	0.153
PAMPA:	0.09 ? 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%):	0.154	30% Bioavailability (F30%):	0.312
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.38
Plasma Protein Binding (PPB):	93.989%	Volume Distribution (VD):	0.49
Fu:	8.107% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.898
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.011	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.445 ? 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):

17.351

Half-life (T1/2):

1.583

ADMET: Toxicity

hERG Blockers:	0.133	hERG Blockers (10um):	0.377
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.451
AMES Toxicity:	0.171	Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.779	Skin Sensitization:	0.988
Carcinogencity:	0.815	Eye Corrosion:	0.374
Eye Irritation:	0.901	Respiratory Toxicity:	0.292
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.462
Hematotoxicity:	0.067	Drug-induced Nephrotoxicity:	0.353
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.285	Hek293 Cytotoxicity:	0.649
BCF:	2.498 ? 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:	3.95 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.783 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.588 ? 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
NPO19920	Yucca gloriosa	Species	Asparagaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(89)80212-2]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[11045899]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17846565]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[19555186]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718054]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21870828]
NPO21735	Clausena anisum-olens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368606]
NPO21635	Pandalus borealis	Species	Pandalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3349210]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	Latex	n.a.	n.a.	PMID[6481361]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22938	Genista hystrix	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19380	Styela plicata	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22246	Aplidium longithorax	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20042	Ambrosia cumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25227	Senecio roseus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20182	Euonymus pendulus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14364	Alisma plantago-aquatica	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7217	Plakobranchus ocellatus	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18197	Cadlina luteomarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20677	Fraxinus angustifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23056	Isaria japonica	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20358	Streptomyces maritimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9972	Angostura granulosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27833	Xerotus discolor	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19380	Styela plicata	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21246	Helichrysum anomalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19693	Lobaria oregana	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23056	Isaria japonica	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23133	Gypsophila patrini	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22187	Ostrea virginica	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22993	Veronica hederifolia	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22938	Genista hystrix	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23094	Pectinophora gossypiella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22453	Befaria racemosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22321	Euphorbia lamprocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20358	Streptomyces maritimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22119	Echinops bannaticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22697	Licaria mahuba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17898	Buckiella undulata	Species	Hypnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14211	Acinetobacter junii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12005	Amomum zambesiacum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18197	Cadlina luteomarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20182	Euonymus pendulus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18568	Artemisia aucheri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21735	Clausena anisum-olens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20042	Ambrosia cumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23475	Psoralea acaulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17819	Ferula transiliensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23176	Schefflera bodinieri	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19920	Yucca gloriosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22881	Cryptotermes brevis	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7217	Plakobranchus ocellatus	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20506	Batatas edulis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17092	Viguiera dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20677	Fraxinus angustifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22246	Aplidium longithorax	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21997	Benzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21635	Pandalus borealis	Species	Pandalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25227	Senecio roseus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15934	Rhododendron ponticum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14364	Alisma plantago-aquatica	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5927	Cortinarius venetus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21874	Cercospora melonis	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	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
Inhibition	10
IC50	9
Ki	2
Activity	7

Activity Type	# Activity
Cell line	14
Individual protein	10
Organism	3
Single protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	IC50	=	104.71	nM	PMID[23571415]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Ki	=	80.0	nM	PMID[23571415]
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	25.69	%	PMID[23571415]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-2.96	%	PMID[23062825]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	50.78	%	PMID[23571415]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	245.47	nM	PMID[23571415]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Ki	=	130.0	nM	PMID[23571415]
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	12.36	%	DOI[10.6019/CHEMBL4495564]
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	5.04	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	-10.31	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-3.09	%	PMID[23062825]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell line	THP-1	Homo sapiens	IC50	=	3300.0	nM	PMID[20561785]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	40340.0	nM	PMID[28038327]
NPT1872	Cell line	Bcap37	Homo sapiens	IC50	>	100000.0	nM	PMID[28038327]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	49230.0	nM	PMID[28038327]
NPT380	Cell line	U-251	Homo sapiens	IC50	>	100000.0	nM	PMID[28038327]
NPT81	Cell line	A549	Homo sapiens	IC50	=	38150.0	nM	PMID[28038327]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	3.3	%	PMID[30006165]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	68.15	%	PMID[29635167]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	70.96	%	PMID[29635167]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	71.27	%	PMID[29635167]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	58.9	%	PMID[30006165]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	79.2	%	PMID[30006165]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	2.33	%	DOI[10.21203/rs.3.rs-23951/v1]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.04	%	DOI[10.6019/CHEMBL4495565]
NPT20904	Cell line	Hep 3B2	Homo sapiens	IC50	>	100000.0	nM	PMID[28038327]

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 NPC248944 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	24507
0.1-0.2	23364
0.2-0.3	1655
0.3-0.4	169
0.4-0.5	98
0.5-0.6	38
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC7479
1.0	High Similarity	NPC257296
0.8	Intermediate Similarity	NPC481427
0.7797	Intermediate Similarity	NPC296734
0.7627	Intermediate Similarity	NPC227260
0.7619	Intermediate Similarity	NPC161035
0.7619	Intermediate Similarity	NPC170438
0.6613	Remote Similarity	NPC24556
0.6406	Remote Similarity	NPC273290
0.6406	Remote Similarity	NPC232044
0.6389	Remote Similarity	NPC144790
0.6389	Remote Similarity	NPC149400
0.6389	Remote Similarity	NPC88962
0.6364	Remote Similarity	NPC305808
0.6351	Remote Similarity	NPC473774
0.6351	Remote Similarity	NPC481418
0.6351	Remote Similarity	NPC481419
0.6351	Remote Similarity	NPC481417
0.6324	Remote Similarity	NPC235126
0.6324	Remote Similarity	NPC242419
0.6301	Remote Similarity	NPC277715
0.6267	Remote Similarity	NPC24960
0.5775	Remote Similarity	NPC177818
0.5732	Remote Similarity	NPC473616
0.5679	Remote Similarity	NPC131693
0.5679	Remote Similarity	NPC485591
0.5679	Remote Similarity	NPC475436
0.5556	Remote Similarity	NPC297348
0.5556	Remote Similarity	NPC325828
0.5556	Remote Similarity	NPC249204
0.5556	Remote Similarity	NPC48339
0.5556	Remote Similarity	NPC177834
0.5556	Remote Similarity	NPC141769
0.5556	Remote Similarity	NPC477547
0.5542	Remote Similarity	NPC312678
0.5542	Remote Similarity	NPC253268
0.5488	Remote Similarity	NPC234352
0.5479	Remote Similarity	NPC486119
0.5422	Remote Similarity	NPC477451
0.5362	Remote Similarity	NPC155985
0.5362	Remote Similarity	NPC601115
0.5357	Remote Similarity	NPC250393
0.5316	Remote Similarity	NPC481420
0.5316	Remote Similarity	NPC481421
0.5301	Remote Similarity	NPC294686
0.5294	Remote Similarity	NPC206003
0.5294	Remote Similarity	NPC473610
0.5244	Remote Similarity	NPC481424
0.5244	Remote Similarity	NPC481422
0.5244	Remote Similarity	NPC481423
0.5233	Remote Similarity	NPC211354
0.5233	Remote Similarity	NPC107188
0.5233	Remote Similarity	NPC19400
0.5211	Remote Similarity	NPC187159
0.5176	Remote Similarity	NPC222731
0.5172	Remote Similarity	NPC264101
0.5114	Remote Similarity	NPC107962
0.5067	Remote Similarity	NPC100451
0.506	Remote Similarity	NPC181845
0.5056	Remote Similarity	NPC6295

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC248944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7317
0.1-0.2	1743
0.2-0.3	66
0.3-0.4	13
0.4-0.5	6
0.5-0.6	2
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6928	Phase 2
0.5584	Remote Similarity	NPD7991	Discontinued
0.5556	Remote Similarity	NPD8171	Phase 2

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