NPASS Compound

Natural Product: NPC217901

Natural Product ID	NPC217901
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Simplexin
IUPAC Name	n.a.
Synonyms	Simplexin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444290
PubChem CID	119045
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

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 82 87 0 0 0 0 0 0 0 0999 V2000 8.1341 -1.1426 0.6376 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2974 0.1250 0.7096 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5580 0.1839 2.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7571 1.4398 2.0926 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7568 1.5306 0.9814 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8063 0.3774 1.0499 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8089 0.4484 -0.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0026 1.6845 -0.0161 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9971 1.7608 -1.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0550 0.7042 -1.1061 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9039 0.9382 -2.2164 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6615 -0.2256 -2.2221 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6736 -1.2649 -1.8941 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4043 -0.5474 -1.3389 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2796 -2.1820 -0.8523 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4278 -1.3906 0.4253 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8807 0.0348 0.1860 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7676 0.8319 0.0839 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6950 0.0071 -1.0829 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4802 1.2267 -1.3839 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3053 2.4127 -0.6433 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5693 1.6285 -0.6660 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9431 1.1773 0.6660 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1381 0.1146 1.3021 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6889 0.5002 1.3691 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2154 0.0490 2.6789 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2506 -0.1590 3.4635 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4932 0.1265 2.7720 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6347 0.3421 3.2546 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2420 -0.6287 4.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3907 -1.1670 0.8896 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2867 0.7432 0.6405 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6244 2.5298 -1.3298 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8390 1.8922 -1.3998 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1211 -1.4968 1.1611 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1834 -1.9898 -3.0696 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4769 -1.6848 -4.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7659 -3.1735 -2.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8039 -1.0600 -0.2328 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4223 -1.9766 0.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7023 -1.2596 1.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5169 0.1125 -0.1013 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8834 1.0453 0.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9550 -0.7416 2.0951 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3164 0.1833 2.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1749 1.4261 3.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3865 2.3544 2.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1580 2.4820 1.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2516 1.6308 -0.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2354 0.4469 2.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2949 -0.6226 1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2496 -0.4977 -0.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3988 0.5248 -1.0716 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4519 1.7576 0.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6364 2.6200 -0.0066 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5246 2.7867 -1.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4978 1.8092 -2.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2331 -0.3611 -3.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2090 -2.6095 -1.2242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5672 -3.0126 -0.6777 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2016 -1.9522 1.0268 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3225 -0.9018 -1.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4606 1.4902 -2.4920 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9561 2.0633 1.3671 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6864 1.6331 1.4384 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2027 -0.0913 2.9826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0942 -0.2275 5.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2278 -1.7328 4.8479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3151 -0.3173 5.4080 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7708 -1.7683 1.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3557 -0.2170 0.5082 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7518 3.4100 -0.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2508 2.8658 -2.3212 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8919 1.1785 -2.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2177 -2.0760 2.1268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3446 -0.5191 1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6384 -2.1161 0.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0496 -2.3054 -5.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1076 -0.8530 -4.6022 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1384 -4.0723 -2.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4464 -2.9730 -2.0408 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3822 -3.3128 -3.8039 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 7 8 1 0 8 9 1 0 10 9 1 1 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 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 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 27 30 1 0 24 31 1 6 23 32 1 0 22 33 1 6 33 34 1 0 16 35 1 0 13 36 1 6 36 37 2 0 36 38 1 0 14 10 1 0 25 17 1 0 18 10 1 0 22 20 1 0 28 24 1 0 19 12 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 2 43 1 0 3 44 1 0 3 45 1 0 4 46 1 0 4 47 1 0 5 48 1 0 5 49 1 0 6 50 1 0 6 51 1 0 7 52 1 0 7 53 1 0 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 12 58 1 6 15 59 1 0 15 60 1 0 16 61 1 1 19 62 1 1 20 63 1 6 23 64 1 1 25 65 1 1 26 66 1 0 30 67 1 0 30 68 1 0 30 69 1 0 31 70 1 0 32 71 1 0 33 72 1 0 33 73 1 0 34 74 1 0 35 75 1 0 35 76 1 0 35 77 1 0 37 78 1 0 37 79 1 0 38 80 1 0 38 81 1 0 38 82 1 0 M END

Standard InCHIKey	JAQJQYMDHBSCKO-JDVVNZBPSA-N
Standard InCHI	InChI=1S/C30H44O8/c1-6-7-8-9-10-11-12-13-28-36-23-21-24-27(16-31,35-24)25(33)29(34)20(14-18(4)22(29)32)30(21,38-28)19(5)15-26(23,37-28)17(2)3/h14,19-21,23-25,31,33-34H,2,6-13,15-16H2,1,3-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28-,29-,30+/m1/s1
SMILES	CCCCCCCCC[C@@]12O[C@H]3[C@@](O1)(C[C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	532.3	Volume:	538.51 ? Van der Waals volume.
Dense:	0.988	LogP:	4.261 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.789 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.527 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	26.0
TPSA:	117.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.223	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.456	Fsp³:	0.833
MCE-18:	102.327 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.381	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.146	Promiscuous compounds:	0.228

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.003	MDCK Permeability:	-4.638
Pgp-inhibitor:	0.0	Pgp-substrate:	0.01
PAMPA:	0.097 ? 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):	0.025
20% Bioavailability (F20%):	0.763	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915	MRP1:	0.998
Plasma Protein Binding (PPB):	95.452%	Volume Distribution (VD):	0.631
Fu:	5.206% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.02
BSEP inhibitor:	0.879

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.806
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.346	CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.135	CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.96
HLM stability:	0.173 ? 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):

6.224

Half-life (T1/2):

0.746

ADMET: Toxicity

hERG Blockers:	0.151	hERG Blockers (10um):	0.764
Human Hepatotoxicity (H-HT):	0.179	Drug-induced Liver Injury (DILI):	0.758
AMES Toxicity:	0.885	Rat Oral Acute Toxicity:	0.685
Maximum Recommended Daily Dose:	0.149	Skin Sensitization:	1.0
Carcinogencity:	0.531	Eye Corrosion:	0.083
Eye Irritation:	0.888	Respiratory Toxicity:	0.25
Drug-induced Neurotoxicity:	0.269	Ototoxicity:	0.741
Hematotoxicity:	0.393	Drug-induced Nephrotoxicity:	0.215
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.216
A549 Cytotoxicity:	0.823	Hek293 Cytotoxicity:	0.884
BCF:	2.323 ? 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:	5.125 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.121 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.848 ? 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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	flower	n.a.	PMID[21916433]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[23558238]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228307]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31150241]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31860304]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223193]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770847]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9756	Daphne genkwa	Species	Thymelaeaceae	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
ED50	1
IC50	11
EC50	1
CC50	1
Ratio CC50/EC50	1
Activity	10
Survival	2

Activity Type	# Activity
Cell line	12
Organism	13
Non-molecular	1
Others	1

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
NPT168	Cell line	P388	Mus musculus	ED50	=	0.005	ug ml-1	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[19674905]
NPT466	Cell line	U-937	Homo sapiens	IC50	>	50000.0	nM	PMID[17958396]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[1904476]
NPT453	Cell line	HT-1080	Homo sapiens	IC50	<	100.0	nM	PMID[22037378]
NPT81	Cell line	A549	Homo sapiens	IC50	=	26960.0	nM	PMID[18280170]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	50000.0	nM	PMID[20485427]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	38820.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	25410.0	nM	PMID[18841906]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	21720.0	nM	PMID[23327905]
NPT81	Cell line	A549	Homo sapiens	IC50	=	0.3	nM	PMID[22551062]
NPT25	Cell line	MT4	Homo sapiens	CC50	>=	18800.0	nM	PMID[23806110]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	10650.0	nM	PMID[23558238]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	47.0	nM	PMID[12542359]
NPT2	Others	Unspecified	n.a.	Ratio CC50/EC50	>=	400.0	n.a.	PMID[22316191]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.0	%	PMID[8277313]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.0	%	PMID[8691203]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	71.0	%	PMID[8691203]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	54.0	%	PMID[3236005]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.6	n.a.	PMID[3236005]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.2	n.a.	PMID[18942825]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3.0	n.a.	PMID[22330636]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.7	n.a.	PMID[18942825]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	100.0	%	PMID[18942825]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	93.0	%	PMID[25856683]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.013	nmol	PMID[8158155]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	77.0	/nmol	PMID[24992637]

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 NPC217901 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	15833
0.1-0.2	32472
0.2-0.3	1438
0.3-0.4	30
0.4-0.5	38
0.5-0.6	29
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475273
1.0	High Similarity	NPC168849
1.0	High Similarity	NPC611341
0.726	Intermediate Similarity	NPC162495
0.6974	Remote Similarity	NPC474508
0.6974	Remote Similarity	NPC473485
0.6974	Remote Similarity	NPC171411
0.6974	Remote Similarity	NPC485701
0.6842	Remote Similarity	NPC251564
0.6842	Remote Similarity	NPC477189
0.6486	Remote Similarity	NPC608985
0.6463	Remote Similarity	NPC605479
0.64	Remote Similarity	NPC605473
0.64	Remote Similarity	NPC610597
0.6316	Remote Similarity	NPC142882
0.6316	Remote Similarity	NPC608716
0.6316	Remote Similarity	NPC609033
0.6136	Remote Similarity	NPC486154
0.5663	Remote Similarity	NPC180902
0.5581	Remote Similarity	NPC475139
0.5529	Remote Similarity	NPC182266
0.5529	Remote Similarity	NPC475154
0.5529	Remote Similarity	NPC485700
0.5476	Remote Similarity	NPC485693
0.5432	Remote Similarity	NPC329008
0.5432	Remote Similarity	NPC317635
0.5432	Remote Similarity	NPC146310
0.5432	Remote Similarity	NPC485696
0.5412	Remote Similarity	NPC223356
0.5412	Remote Similarity	NPC298697
0.5412	Remote Similarity	NPC475500
0.5412	Remote Similarity	NPC100017
0.5412	Remote Similarity	NPC481742
0.5357	Remote Similarity	NPC475314
0.5357	Remote Similarity	NPC102997
0.5349	Remote Similarity	NPC75831
0.5349	Remote Similarity	NPC471137
0.5287	Remote Similarity	NPC471136
0.5287	Remote Similarity	NPC116727
0.5287	Remote Similarity	NPC39509
0.5227	Remote Similarity	NPC481744
0.5227	Remote Similarity	NPC481743
0.5176	Remote Similarity	NPC324104
0.5176	Remote Similarity	NPC473548
0.5119	Remote Similarity	NPC475606
0.5111	Remote Similarity	NPC475548
0.5111	Remote Similarity	NPC485698

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC217901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6253
0.1-0.2	2869
0.2-0.3	27
0.3-0.4	1
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