NPASS Compound

Natural Product: NPC475232

Natural Product ID	NPC475232
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Trans-Murisolinone
IUPAC Name	(3R,5S)-5-[(11R)-11-hydroxy-11-[(2R,5R)-5-[(1R)-1-hydroxydodecyl]oxolan-2-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one
Synonyms	Trans-Murisolinone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501502
PubChem CID	44559891
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 102103 0 0 0 0 0 0 0 0999 V2000 -12.6782 -0.1473 1.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5112 1.2871 1.7536 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1183 1.8042 1.8889 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2258 1.7301 0.7171 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8279 0.4062 0.1957 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0336 -0.4246 1.1789 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7379 0.2567 1.5651 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8167 0.5065 0.3986 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4399 -0.7882 -0.3040 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7444 -1.6898 0.6377 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4556 -1.2527 1.2289 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2865 -1.0857 0.3872 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1249 -0.1931 -0.7319 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1588 1.2677 -0.5973 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9217 1.5741 0.2119 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0183 0.4414 -0.2237 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7339 -0.3268 -1.1295 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2158 1.0329 -0.9348 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0603 -0.1331 -1.3181 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3331 0.1884 -2.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2579 1.0598 -1.2175 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6819 0.5125 0.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3653 -0.7395 0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6652 -1.1604 -0.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0343 -1.3852 -1.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0400 -0.3686 -2.6126 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8081 0.8690 -2.5260 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2663 0.9423 -2.4880 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0918 0.4195 -1.3995 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0189 -0.9212 -1.1094 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1468 -1.1668 0.2655 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9970 -2.3302 0.7113 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4531 0.1072 0.9346 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9435 1.1397 -0.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9279 0.2692 1.1665 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4231 -0.8120 2.0341 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6787 -1.6276 2.5077 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8804 -0.8998 2.3332 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2473 1.8024 -1.9743 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9708 -2.4036 -0.1173 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.5772 -0.5236 1.9978 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8541 -0.7629 1.7549 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9049 -0.2532 0.3178 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9758 1.4286 2.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1112 1.9052 1.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6876 1.3217 2.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2387 2.9000 2.1794 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3158 2.3903 0.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7698 2.2502 -0.1410 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1093 0.6078 -0.6605 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6395 -0.1904 -0.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8671 -1.4087 0.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6055 -0.5596 2.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2113 -0.3078 2.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9750 1.2542 1.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2092 1.2400 -0.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8803 0.9174 0.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8042 -0.5283 -1.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3543 -1.2599 -0.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5840 -2.6727 0.0919 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4152 -1.9610 1.5227 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2439 -2.0338 2.0507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7050 -0.3607 1.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3955 -0.9727 1.1230 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6395 -0.4865 -1.6900 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0461 1.7787 -0.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9173 1.6812 -1.6313 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0991 1.5768 1.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5254 2.5621 -0.0646 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6458 -0.1647 0.6535 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7197 1.6251 -0.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2067 -0.7582 -0.4130 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4553 -0.7773 -2.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1059 0.7097 -2.9632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8247 -0.7641 -2.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6649 2.0166 -0.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0632 1.4320 -1.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3687 1.3316 0.5261 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8144 0.5979 0.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3897 -0.8689 1.4455 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6561 -1.6413 0.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4161 -0.4128 0.3036 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9910 -2.1169 0.4107 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8850 -2.1328 -1.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1800 -2.1502 -1.9621 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4999 -0.9671 -3.5580 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9997 -0.2232 -3.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4380 1.4156 -1.5683 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4205 1.5598 -3.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5328 2.0704 -2.6159 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7067 0.5604 -3.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2155 0.5719 -1.7093 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8696 0.1416 1.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9037 1.3799 0.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6334 2.0217 -0.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4026 0.2346 0.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1334 1.2836 1.5908 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1173 -0.6850 3.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4597 -0.1499 1.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2616 -1.9021 2.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7698 1.3109 -2.6359 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4966 -2.4359 -0.9704 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 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 18 39 1 0 12 40 1 0 17 13 1 0 34 29 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 5 50 1 0 5 51 1 0 6 52 1 0 6 53 1 0 7 54 1 0 7 55 1 0 8 56 1 0 8 57 1 0 9 58 1 0 9 59 1 0 10 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 12 64 1 1 13 65 1 6 14 66 1 0 14 67 1 0 15 68 1 0 15 69 1 0 16 70 1 1 18 71 1 1 19 72 1 0 19 73 1 0 20 74 1 0 20 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 23 80 1 0 23 81 1 0 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 26 86 1 0 26 87 1 0 27 88 1 0 27 89 1 0 28 90 1 0 28 91 1 0 29 92 1 6 33 93 1 1 34 94 1 0 34 95 1 0 35 96 1 0 35 97 1 0 38 98 1 0 38 99 1 0 38100 1 0 39101 1 0 40102 1 0 M END

Standard InCHIKey	USFLRIYXFWLSMW-HNTSJLFCSA-N
Standard InCHI	InChI=1S/C34H62O6/c1-3-4-5-6-7-8-12-15-18-21-30(36)32-23-24-33(40-32)31(37)22-19-16-13-10-9-11-14-17-20-29-26-28(25-27(2)35)34(38)39-29/h28-33,36-37H,3-26H2,1-2H3/t28-,29-,30+,31+,32+,33+/m0/s1
SMILES	CCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CCCCCCCCCC[C@@H]1OC(=O)[C@H](C1)CC(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	566.45	Volume:	626.975 ? Van der Waals volume.
Dense:	0.903	LogP:	6.553 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.337 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.898 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	12.0
TPSA:	93.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.345	Fsp³:	0.941
MCE-18:	30.97 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.749	Fluc inhibitor:	0.041 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.596	Promiscuous compounds:	0.41

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.095	MDCK Permeability:	-4.847
Pgp-inhibitor:	0.0	Pgp-substrate:	0.052
PAMPA:	0.023 ? 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):	0.242
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.988
Plasma Protein Binding (PPB):	98.421%	Volume Distribution (VD):	1.079
Fu:	1.877% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.424
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.013
BSEP inhibitor:	0.724

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.026	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.382	CYP2D6-substrate:	0.688
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.787
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.949
HLM stability:	0.0 ? 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):

4.2

Half-life (T1/2):

1.317

ADMET: Toxicity

hERG Blockers:	0.346	hERG Blockers (10um):	0.604
Human Hepatotoxicity (H-HT):	0.553	Drug-induced Liver Injury (DILI):	0.352
AMES Toxicity:	0.034	Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.34	Skin Sensitization:	0.999
Carcinogencity:	0.128	Eye Corrosion:	0.717
Eye Irritation:	0.987	Respiratory Toxicity:	0.875
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.303
Hematotoxicity:	0.194	Drug-induced Nephrotoxicity:	0.581
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.642	Hek293 Cytotoxicity:	0.073
BCF:	0.97 ? 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:	5.01 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.301 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.126 ? 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
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11087592]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15730242]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1593281]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30028612]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8676130]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946743]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7697	Asimina triloba	Species	Annonaceae	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	6

Activity Type	# Activity
Cell line	6

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	2.76	10'-2 ug/ml	PMID[21560225]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.96	10'-2 ug/ml	PMID[21560225]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.16	ug ml-1	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	ED50	=	1.23	ug ml-1	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	2.14	10'-1 ug/ml	PMID[18242997]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	5.9	10'-3 ug/ml	PMID[18242997]

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
-	Artemia	LC50	=	18.2	ug.mL-1	PMID[21560225]

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 NPC475232 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	15713
0.1-0.2	30526
0.2-0.3	3279
0.3-0.4	123
0.4-0.5	160
0.5-0.6	31
0.6-0.7	1
0.7-0.8	0
0.8-0.85	2
0.85-0.9	6
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474100
0.9302	High Similarity	NPC482767
0.9302	High Similarity	NPC475260
0.9302	High Similarity	NPC488621
0.9302	High Similarity	NPC473775
0.9302	High Similarity	NPC488622
0.9091	High Similarity	NPC475616
0.8889	High Similarity	NPC473699
0.8889	High Similarity	NPC480251
0.8889	High Similarity	NPC51249
0.8889	High Similarity	NPC480250
0.8864	High Similarity	NPC480078
0.8864	High Similarity	NPC480071
0.8125	Intermediate Similarity	NPC480076
0.8125	Intermediate Similarity	NPC480077
0.7917	Intermediate Similarity	NPC480075
0.7826	Intermediate Similarity	NPC488234
0.7692	Intermediate Similarity	NPC475206
0.75	Intermediate Similarity	NPC473791
0.6042	Remote Similarity	NPC480074
0.58	Remote Similarity	NPC480072
0.5357	Remote Similarity	NPC20621
0.5357	Remote Similarity	NPC318963
0.5357	Remote Similarity	NPC605101
0.5273	Remote Similarity	NPC241360
0.5273	Remote Similarity	NPC293136
0.5192	Remote Similarity	NPC606043
0.5179	Remote Similarity	NPC485252
0.5098	Remote Similarity	NPC73310
0.5098	Remote Similarity	NPC473529
0.5098	Remote Similarity	NPC180363
0.5098	Remote Similarity	NPC94875
0.5098	Remote Similarity	NPC11332
0.5098	Remote Similarity	NPC145914
0.5098	Remote Similarity	NPC601174
0.5098	Remote Similarity	NPC601403
0.5098	Remote Similarity	NPC603568
0.5098	Remote Similarity	NPC604330
0.5098	Remote Similarity	NPC608300
0.5098	Remote Similarity	NPC611200
0.5098	Remote Similarity	NPC611571
0.5094	Remote Similarity	NPC107986
0.5094	Remote Similarity	NPC223871
0.5094	Remote Similarity	NPC231009
0.5094	Remote Similarity	NPC103284
0.5094	Remote Similarity	NPC110710
0.5094	Remote Similarity	NPC1083
0.5094	Remote Similarity	NPC82795
0.5094	Remote Similarity	NPC286338
0.5094	Remote Similarity	NPC603931
0.5094	Remote Similarity	NPC604237

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5818
0.1-0.2	3212
0.2-0.3	118
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