NPASS Compound

Natural Product: NPC238829

Natural Product ID	NPC238829
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KYELXPJVGNZIGC-GKFGJCLESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	161294
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002728] Jerveratrum-type alkaloids

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 73 78 0 0 0 0 0 0 0 0999 V2000 6.8863 2.5013 0.3265 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1734 1.1654 0.3073 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8431 1.2871 1.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0926 0.0245 0.8307 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8414 -0.0276 -0.6864 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7939 -1.0940 -0.7142 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4573 -2.4165 -0.5096 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9797 -0.6922 0.4996 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2546 -1.8416 1.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1529 -2.3565 0.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7135 -1.3759 -0.3940 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2699 0.0449 -0.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9546 0.3564 0.1774 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2623 1.8073 0.3041 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4726 0.8382 -0.6136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6229 -0.0974 -0.6746 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1085 -1.2745 0.1705 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9807 -2.4345 -0.1144 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3850 -2.0624 0.2318 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1150 -2.8415 0.8593 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9029 -0.7414 -0.1852 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1742 -0.3700 0.5416 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7498 0.8488 -0.1486 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8402 1.4129 -1.1909 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4467 1.6223 -0.6353 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8757 0.3674 -0.0265 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6533 0.5463 1.4732 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9795 1.8470 0.8249 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8739 -0.1008 1.4078 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1078 -0.4016 -1.2587 N 0 0 0 0 0 4 0 0 0 0 0 0 5.9529 0.8008 -1.1383 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9655 2.2876 0.5298 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8265 3.0197 -0.6568 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4823 3.1897 1.0892 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7608 0.3773 0.8197 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3349 2.1654 0.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 1.4917 2.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7990 -0.8201 1.0869 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5228 0.9312 -1.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1700 -1.0744 -1.6264 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8362 -2.5216 0.5211 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8255 -3.3025 -0.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2954 -2.5247 -1.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 -1.4793 2.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9669 -2.6859 1.3141 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5166 -2.9720 0.9603 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4623 -3.1149 -0.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8310 -1.5612 -1.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0168 1.9144 1.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5964 2.2712 -0.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3861 2.3925 0.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6584 1.6923 0.0551 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3293 1.2827 -1.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8126 -0.5221 -1.6782 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0611 -0.9893 1.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7014 -3.2731 0.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8809 -2.7237 -1.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1881 -0.8455 -1.2703 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9968 -0.1771 1.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8885 -1.1917 0.4539 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7293 0.6290 -0.6162 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8480 0.8729 -2.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2248 2.4475 -1.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5321 2.3854 0.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7891 2.0536 -1.4151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8778 -0.3597 2.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3949 1.3264 1.7885 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6539 0.9714 1.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8009 2.7307 0.4344 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6198 -1.1107 -0.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0821 -0.6656 -2.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9361 0.5022 -1.5504 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5672 1.6378 -1.7190 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 2 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 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 1 23 28 1 0 8 29 1 1 5 30 1 0 30 31 1 0 31 2 1 0 29 4 1 0 13 8 1 0 26 16 1 0 17 11 1 0 26 21 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 1 3 36 1 0 3 37 1 0 4 38 1 1 5 39 1 6 6 40 1 6 7 41 1 0 7 42 1 0 7 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 6 14 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 6 17 55 1 1 18 56 1 0 18 57 1 0 21 58 1 6 22 59 1 0 22 60 1 0 23 61 1 6 24 62 1 0 24 63 1 0 25 64 1 0 25 65 1 0 27 66 1 0 27 67 1 0 27 68 1 0 28 69 1 0 30 70 1 0 30 71 1 0 31 72 1 0 31 73 1 0 M CHG 1 30 1 M END

Standard InCHIKey	KYELXPJVGNZIGC-GKFGJCLESA-N
Standard InCHI	InChI=1S/C27H41NO3/c1-14-9-24-25(28-13-14)16(3)27(31-24)8-6-18-19(15(27)2)11-21-20(18)12-23(30)22-10-17(29)5-7-26(21,22)4/h14,16-18,20-22,24-25,28-29H,5-13H2,1-4H3/p+1/t14-,16+,17-,18+,20-,21-,22+,24+,25-,26+,27-/m0/s1
SMILES	C[C@H]1C[C@@H]2[C@H]([C@@H](C)[C@@]3(CC[C@@H]4C(=C3C)C[C@H]3[C@H]4CC(=O)[C@H]4C[C@H](CC[C@]34C)O)O2)[NH2+]C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	427.31	Volume:	456.304 ? Van der Waals volume.
Dense:	0.936	LogP:	3.26 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.179 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.235 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	31.0
TPSA:	58.56 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.567	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.638	Fsp³:	0.889
MCE-18:	136.235 ? 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:	0.893	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.004	Promiscuous compounds:	0.468

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.017	MDCK Permeability:	-4.987
Pgp-inhibitor:	0.029	Pgp-substrate:	0.209
PAMPA:	0.619 ? 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%):	0.003	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.178

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025	MRP1:	0.893
Plasma Protein Binding (PPB):	57.467%	Volume Distribution (VD):	0.083
Fu:	48.339% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.919
OATP1B3 inhibitor:	0.246	BCRP inhibitor:	0.009
BSEP inhibitor:	0.798

ADMET: Metabolism

CYP1A2-inhibitor:	0.014	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.952	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.973	CYP3A4-substrate:	0.418
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.069
HLM stability:	0.362 ? 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):

15.601

Half-life (T1/2):

1.756

ADMET: Toxicity

hERG Blockers:	0.081	hERG Blockers (10um):	0.327
Human Hepatotoxicity (H-HT):	0.751	Drug-induced Liver Injury (DILI):	0.464
AMES Toxicity:	0.589	Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.923	Skin Sensitization:	0.986
Carcinogencity:	0.822	Eye Corrosion:	0.004
Eye Irritation:	0.238	Respiratory Toxicity:	0.729
Drug-induced Neurotoxicity:	0.583	Ototoxicity:	0.774
Hematotoxicity:	0.315	Drug-induced Nephrotoxicity:	0.839
Genotoxicity:	0.422	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.576	Hek293 Cytotoxicity:	0.499
BCF:	0.711 ? 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:	3.372 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.928 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.239 ? 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
NPO64796	Fritillaria unibracteata var. wabuensis + Fusarium sp. symbiont	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[ 21958967]
NPO64706	Fritillaria unibracteata var. wabuensis + Fusarium redolens symbiont	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[ 25869849]
NPO26833	Ichnocarpus frutescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1158	Isochrysis galbana	Species	Isochrysidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10290	Fritillaria ebeiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10290.1	Fritillaria ebeiensis var. purpurea	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12556	Fritillaria verticillata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25808.1	Fritillaria taipaiensis var. ningxiaensis	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26065	Elaeocarpus archboldianus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25253	Corydalis caseana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12867	Fritillaria siechuanica	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14347	Fritillaria anhuiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23477	Anabaena torulosa	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12867	Fritillaria siechuanica	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10290.1	Fritillaria ebeiensis var. purpurea	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14347	Fritillaria anhuiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10290	Fritillaria ebeiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25808.1	Fritillaria taipaiensis var. ningxiaensis	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12867	Fritillaria siechuanica	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25808.1	Fritillaria taipaiensis var. ningxiaensis	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10290	Fritillaria ebeiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14347	Fritillaria anhuiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10290.1	Fritillaria ebeiensis var. purpurea	Varieties	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25334	Bulbus fritillariae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12556	Fritillaria verticillata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14347	Fritillaria anhuiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14135	Fritillaria prezewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12556	Fritillaria verticillata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4487	Fritillaria thunbergii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26096	Jatropha multiloba	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1158	Isochrysis galbana	Species	Isochrysidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10290	Fritillaria ebeiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26833	Ichnocarpus frutescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25808	Fritillaria taipaiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7844	Fritillaria hupehensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26282	Phebalium ovatifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23477	Anabaena torulosa	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5648	Fritillaria ussuriensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1279	Fritillaria cirrhosa	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12556	Fritillaria verticillata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26765	Litsea pedunculata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18644	Fritillaria walujewii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25749	Kielmeyera argentea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25253	Corydalis caseana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25941	Garcinia yunnanensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14347	Fritillaria anhuiensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28973	Rhytisma fulvum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22292	Fritillaria przewalskii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26065	Elaeocarpus archboldianus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14849	Fritillaria unibracteata	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26340	Chione venosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12273	Fritillaria delavayi	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25300	Senecio ruderalis	Species	Asteraceae	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
Activity	4
CC50	4

Activity Type	# Activity
Cell line	8

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
NPT1635	Cell line	H9c2	Rattus norvegicus	Activity	=	72.0	%	PMID[38294199]
NPT113	Cell line	RAW264.7	Mus musculus	Activity	=	66.0	%	PMID[38294199]
NPT81	Cell line	A549	Homo sapiens	CC50	=	9600.0	nM	PMID[38294199]
NPT397	Cell line	NCI-H460	Homo sapiens	CC50	=	17000.0	nM	PMID[38294199]

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 NPC238829 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	22468
0.1-0.2	25997
0.2-0.3	1368
0.3-0.4	22
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6543	Remote Similarity	NPC28280
0.5882	Remote Similarity	NPC605062

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC238829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7181
0.1-0.2	1872
0.2-0.3	95
0.3-0.4	2
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