NPASS Compound

Natural Product: NPC202055

Natural Product ID	NPC202055
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Membranacin
IUPAC Name	(2S)-4-[(13R)-13-hydroxy-13-[(2S,5R)-5-[(2R,5S)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms	Membranacin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452872
PubChem CID	44593482
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 109111 0 0 0 0 0 0 0 0999 V2000 -11.7696 1.1047 -2.5877 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4534 1.6312 -2.0562 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6448 1.9802 -0.6082 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0828 0.8097 0.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9720 -0.2721 0.1235 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3862 -1.4322 0.9455 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5069 -2.5933 0.9935 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1573 -2.5841 1.5655 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0946 -1.7217 0.9970 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8087 -2.0275 1.8076 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6473 -1.2294 1.3394 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2563 -1.4658 -0.0877 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7675 -2.8841 -0.3136 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2854 -2.6957 -0.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0319 -1.2944 -0.4189 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2293 -0.6462 -0.4940 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1346 -0.5286 0.5337 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2123 -1.1120 0.7324 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1249 0.0926 0.7582 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1935 1.2468 0.6069 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9671 0.7488 0.0083 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8148 2.3271 -0.2879 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8595 3.0407 0.4965 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5600 4.1179 -0.2121 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3613 3.9518 -1.4035 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6243 3.2623 -1.5416 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9569 1.8767 -1.3185 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8585 1.2251 0.0063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6981 1.8416 1.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1453 1.7652 0.8768 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7858 0.4601 1.0526 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5417 -0.7544 0.3074 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7617 -0.8086 -1.1567 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1854 -0.4856 -1.5608 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1593 -1.4129 -0.9589 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1458 -1.0423 -0.1588 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8838 -2.2558 0.2237 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2619 -3.3420 -0.3975 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1971 -2.8580 -1.1356 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3904 -3.5433 -1.8436 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3010 -2.1334 -0.3390 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1865 1.7361 -1.4646 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0397 0.1280 1.4144 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.6221 1.5172 -1.9855 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8453 0.0100 -2.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9035 1.4538 -3.6086 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6380 0.9056 -2.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1364 2.5436 -2.6427 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6573 2.3977 -0.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3854 2.8288 -0.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0296 0.3930 -0.1341 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1188 1.1014 1.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0807 0.2350 0.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9546 -0.5871 -0.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6178 -1.0945 2.0028 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3822 -1.7815 0.5131 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4558 -2.9988 -0.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1311 -3.4343 1.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7764 -3.6683 1.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2298 -2.4059 2.7022 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3271 -0.6445 1.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9597 -1.8375 -0.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0513 -1.6666 2.8447 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6437 -3.1076 1.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8289 -1.3384 2.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1272 -1.2995 -0.7361 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8621 -3.2278 -1.3507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1507 -3.6048 0.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0851 -2.7811 1.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6548 -3.3739 -0.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5533 -1.2743 -1.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6463 -0.5193 1.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2681 -1.6921 1.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4888 -1.8130 -0.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7865 0.1029 -0.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6935 0.0999 1.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0896 1.6480 1.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0422 3.0569 -0.4603 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4125 2.3593 1.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2137 3.6018 1.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1686 4.6862 0.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7473 4.9227 -0.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5906 5.0522 -1.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6604 3.6906 -2.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4346 3.9610 -1.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9339 3.4607 -2.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0455 1.7104 -1.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4010 1.2274 -2.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8706 0.9846 0.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3031 0.1801 -0.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4626 1.2453 2.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3315 2.8660 1.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4668 2.2565 -0.1131 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5939 2.4925 1.6589 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6997 0.1371 2.1792 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9323 0.6471 1.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3876 -1.4944 0.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6431 -1.3644 0.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0802 -0.2899 -1.8077 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6547 -1.9165 -1.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2430 -0.6400 -2.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4363 0.5641 -1.3677 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3609 -0.0394 0.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9190 -2.3479 1.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0167 -1.9679 0.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3882 -1.2428 -1.0249 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5681 -3.0740 -0.8738 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1104 1.4906 -1.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3006 0.4745 0.5280 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 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 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 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 37 41 1 0 22 42 1 0 11 43 1 0 16 12 1 0 21 17 1 0 39 35 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 1 12 66 1 6 13 67 1 0 13 68 1 0 14 69 1 0 14 70 1 0 15 71 1 6 17 72 1 1 18 73 1 0 18 74 1 0 19 75 1 0 19 76 1 0 20 77 1 1 22 78 1 6 23 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 26 85 1 0 26 86 1 0 27 87 1 0 27 88 1 0 28 89 1 0 28 90 1 0 29 91 1 0 29 92 1 0 30 93 1 0 30 94 1 0 31 95 1 0 31 96 1 0 32 97 1 0 32 98 1 0 33 99 1 0 33100 1 0 34101 1 0 34102 1 0 36103 1 0 37104 1 1 41105 1 0 41106 1 0 41107 1 0 42108 1 0 43109 1 0 M END

Standard InCHIKey	URLVCROWVOSNPT-PSYGJSNASA-N
Standard InCHI	InChI=1S/C37H66O6/c1-3-4-5-6-7-13-16-19-22-31(38)33-24-26-35(42-33)36-27-25-34(43-36)32(39)23-20-17-14-11-9-8-10-12-15-18-21-30-28-29(2)41-37(30)40/h28-29,31-36,38-39H,3-27H2,1-2H3/t29-,31-,32+,33-,34-,35+,36+/m0/s1
SMILES	CCCCCCCCCC[C@@H]([C@@H]1CC[C@@H](O1)[C@H]1CC[C@H](O1)[C@@H](CCCCCCCCCCCCC1=C[C@@H](OC1=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	606.49	Volume:	670.307 ? Van der Waals volume.
Dense:	0.905	LogP:	6.998 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.525 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.935 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	85.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.08	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.585	Fsp³:	0.919
MCE-18:	40.563 ? 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:	0.858	Fluc inhibitor:	0.099 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.068 ? 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:	0.582	Promiscuous compounds:	0.354

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.113	MDCK Permeability:	-4.825
Pgp-inhibitor:	0.012	Pgp-substrate:	0.423
PAMPA:	0.001 ? 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):	0.951
20% Bioavailability (F20%):	0.996	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.99
Plasma Protein Binding (PPB):	99.652%	Volume Distribution (VD):	1.366
Fu:	0.988% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.95
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.92
BSEP inhibitor:	0.718

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.022	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.265
CYP2D6-inhibitor:	0.092	CYP2D6-substrate:	0.732
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.007 ? 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):

4.803

Half-life (T1/2):

1.728

ADMET: Toxicity

hERG Blockers:	0.659	hERG Blockers (10um):	0.887
Human Hepatotoxicity (H-HT):	0.739	Drug-induced Liver Injury (DILI):	0.356
AMES Toxicity:	0.449	Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.848	Skin Sensitization:	1.0
Carcinogencity:	0.494	Eye Corrosion:	0.118
Eye Irritation:	0.723	Respiratory Toxicity:	0.958
Drug-induced Neurotoxicity:	0.142	Ototoxicity:	0.425
Hematotoxicity:	0.113	Drug-induced Nephrotoxicity:	0.793
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.092
A549 Cytotoxicity:	0.99	Hek293 Cytotoxicity:	0.453
BCF:	0.725 ? 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:	4.964 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.453 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.45 ? 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
NPO32731	rollinia mucosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10479316]

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	5
Non-molecular	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
NPT81	Cell line	A549	Homo sapiens	ED50	=	4.0	10'-1 ug/ml	PMID[11000015]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.18	ug ml-1	PMID[20189399]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	3.04	ug ml-1	PMID[11000015]
NPT306	Cell line	PC-3	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[19618898]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[24479418]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	<	0.001	ug ml-1	PMID[10479316]

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 salina	LC50	=	0.05	ug.mL-1	PMID[11000015]

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 NPC202055 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	15436
0.1-0.2	30243
0.2-0.3	3806
0.3-0.4	137
0.4-0.5	30
0.5-0.6	46
0.6-0.7	63
0.7-0.8	0
0.8-0.85	16
0.85-0.9	19
0.9-0.95	12
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC25764
1.0	High Similarity	NPC235809
1.0	High Similarity	NPC39279
1.0	High Similarity	NPC39167
1.0	High Similarity	NPC292809
1.0	High Similarity	NPC606804
1.0	High Similarity	NPC607425
1.0	High Similarity	NPC608574
0.9302	High Similarity	NPC473156
0.9302	High Similarity	NPC282815
0.9302	High Similarity	NPC600956
0.9091	High Similarity	NPC473671
0.9091	High Similarity	NPC219652
0.9091	High Similarity	NPC475268
0.9091	High Similarity	NPC473840
0.9091	High Similarity	NPC470400
0.9091	High Similarity	NPC77871
0.9091	High Similarity	NPC9678
0.9091	High Similarity	NPC319036
0.9091	High Similarity	NPC605867
0.8889	High Similarity	NPC132940
0.8864	High Similarity	NPC610454
0.878	High Similarity	NPC73310
0.878	High Similarity	NPC473529
0.878	High Similarity	NPC180363
0.878	High Similarity	NPC94875
0.878	High Similarity	NPC11332
0.878	High Similarity	NPC145914
0.878	High Similarity	NPC601174
0.878	High Similarity	NPC601403
0.878	High Similarity	NPC603568
0.878	High Similarity	NPC604330
0.878	High Similarity	NPC608300
0.878	High Similarity	NPC611200
0.878	High Similarity	NPC611571
0.8696	High Similarity	NPC20533
0.8696	High Similarity	NPC485250
0.8696	High Similarity	NPC605396
0.8667	High Similarity	NPC25703
0.8444	Intermediate Similarity	NPC473649
0.8444	Intermediate Similarity	NPC154097
0.8444	Intermediate Similarity	NPC159750
0.8444	Intermediate Similarity	NPC73248
0.8444	Intermediate Similarity	NPC470401
0.8444	Intermediate Similarity	NPC600524
0.8444	Intermediate Similarity	NPC608355
0.8333	Intermediate Similarity	NPC120398
0.8333	Intermediate Similarity	NPC473995
0.8333	Intermediate Similarity	NPC471567
0.8261	Intermediate Similarity	NPC604764
0.8182	Intermediate Similarity	NPC329829
0.8182	Intermediate Similarity	NPC475159
0.8182	Intermediate Similarity	NPC131002
0.8182	Intermediate Similarity	NPC473780
0.8182	Intermediate Similarity	NPC604521
0.7843	Intermediate Similarity	NPC473520
0.7826	Intermediate Similarity	NPC81045
0.7826	Intermediate Similarity	NPC39754
0.7826	Intermediate Similarity	NPC171135
0.7826	Intermediate Similarity	NPC61257
0.7826	Intermediate Similarity	NPC320569
0.7826	Intermediate Similarity	NPC133730
0.7826	Intermediate Similarity	NPC191929
0.7826	Intermediate Similarity	NPC100454
0.7826	Intermediate Similarity	NPC242364
0.7826	Intermediate Similarity	NPC172821
0.7826	Intermediate Similarity	NPC156804
0.7826	Intermediate Similarity	NPC274446
0.7826	Intermediate Similarity	NPC485251
0.7826	Intermediate Similarity	NPC151403
0.7826	Intermediate Similarity	NPC261952
0.7826	Intermediate Similarity	NPC605171
0.7692	Intermediate Similarity	NPC473905
0.766	Intermediate Similarity	NPC93794
0.766	Intermediate Similarity	NPC473504
0.766	Intermediate Similarity	NPC163093
0.766	Intermediate Similarity	NPC144415
0.766	Intermediate Similarity	NPC81778
0.766	Intermediate Similarity	NPC40066
0.766	Intermediate Similarity	NPC607439
0.766	Intermediate Similarity	NPC608157
0.75	Intermediate Similarity	NPC241360
0.75	Intermediate Similarity	NPC293136
0.7451	Intermediate Similarity	NPC89001
0.7391	Intermediate Similarity	NPC100921
0.7391	Intermediate Similarity	NPC477018
0.7347	Intermediate Similarity	NPC42598
0.7347	Intermediate Similarity	NPC65930
0.72	Intermediate Similarity	NPC329838
0.72	Intermediate Similarity	NPC602738
0.6977	Remote Similarity	NPC609415
0.6923	Remote Similarity	NPC169511
0.6923	Remote Similarity	NPC258068
0.6923	Remote Similarity	NPC287164
0.6923	Remote Similarity	NPC234077
0.6923	Remote Similarity	NPC476583
0.6863	Remote Similarity	NPC329615
0.6809	Remote Similarity	NPC606043
0.6792	Remote Similarity	NPC477014
0.6792	Remote Similarity	NPC477013
0.6667	Remote Similarity	NPC107986
0.6667	Remote Similarity	NPC223871
0.6667	Remote Similarity	NPC231009
0.6667	Remote Similarity	NPC103284
0.6667	Remote Similarity	NPC110710
0.6667	Remote Similarity	NPC1083
0.6667	Remote Similarity	NPC239517
0.6667	Remote Similarity	NPC82795
0.6667	Remote Similarity	NPC286338
0.6667	Remote Similarity	NPC603931
0.6667	Remote Similarity	NPC604237
0.6545	Remote Similarity	NPC91067
0.6538	Remote Similarity	NPC309211
0.6538	Remote Similarity	NPC477010
0.6531	Remote Similarity	NPC488253
0.6531	Remote Similarity	NPC473669
0.6531	Remote Similarity	NPC488251
0.6481	Remote Similarity	NPC480082
0.6429	Remote Similarity	NPC253801
0.6429	Remote Similarity	NPC477015
0.6415	Remote Similarity	NPC477012
0.64	Remote Similarity	NPC232555
0.64	Remote Similarity	NPC171174
0.64	Remote Similarity	NPC114694
0.64	Remote Similarity	NPC485248
0.64	Remote Similarity	NPC142117
0.64	Remote Similarity	NPC480249
0.64	Remote Similarity	NPC485249
0.64	Remote Similarity	NPC240695
0.6316	Remote Similarity	NPC473663
0.6316	Remote Similarity	NPC473723
0.6316	Remote Similarity	NPC475173
0.6275	Remote Similarity	NPC488632
0.6275	Remote Similarity	NPC134865
0.6275	Remote Similarity	NPC103523
0.6275	Remote Similarity	NPC488627
0.6275	Remote Similarity	NPC488631
0.6275	Remote Similarity	NPC477011
0.625	Remote Similarity	NPC280612
0.6182	Remote Similarity	NPC320458
0.6154	Remote Similarity	NPC280621
0.6154	Remote Similarity	NPC48338
0.6154	Remote Similarity	NPC488628
0.6078	Remote Similarity	NPC182383
0.6038	Remote Similarity	NPC178215
0.6038	Remote Similarity	NPC473687
0.6038	Remote Similarity	NPC204686
0.6038	Remote Similarity	NPC219498
0.6038	Remote Similarity	NPC308412
0.6038	Remote Similarity	NPC134885
0.6038	Remote Similarity	NPC488247
0.6038	Remote Similarity	NPC210218
0.6038	Remote Similarity	NPC488248
0.5965	Remote Similarity	NPC322529
0.5926	Remote Similarity	NPC20621
0.5926	Remote Similarity	NPC318963
0.5926	Remote Similarity	NPC134807
0.5926	Remote Similarity	NPC488250
0.5926	Remote Similarity	NPC605101
0.5893	Remote Similarity	NPC488623
0.5893	Remote Similarity	NPC488624
0.5893	Remote Similarity	NPC488629
0.5818	Remote Similarity	NPC473478
0.5818	Remote Similarity	NPC69082
0.5818	Remote Similarity	NPC473651
0.5818	Remote Similarity	NPC488249
0.5818	Remote Similarity	NPC66346
0.575	Remote Similarity	NPC84038
0.5714	Remote Similarity	NPC283085
0.5714	Remote Similarity	NPC132496
0.5714	Remote Similarity	NPC130359
0.5714	Remote Similarity	NPC14901
0.566	Remote Similarity	NPC47937
0.56	Remote Similarity	NPC112685
0.5574	Remote Similarity	NPC477017
0.5574	Remote Similarity	NPC477016
0.5556	Remote Similarity	NPC480079
0.5532	Remote Similarity	NPC608138
0.549	Remote Similarity	NPC228411
0.549	Remote Similarity	NPC480072
0.5455	Remote Similarity	NPC478998
0.5439	Remote Similarity	NPC231096
0.5439	Remote Similarity	NPC475581
0.5439	Remote Similarity	NPC62118
0.5439	Remote Similarity	NPC107717
0.5439	Remote Similarity	NPC488252
0.5439	Remote Similarity	NPC606740
0.5439	Remote Similarity	NPC608614
0.5424	Remote Similarity	NPC488630
0.5424	Remote Similarity	NPC488625
0.5424	Remote Similarity	NPC488626
0.537	Remote Similarity	NPC480078
0.537	Remote Similarity	NPC480071
0.5357	Remote Similarity	NPC600188
0.5345	Remote Similarity	NPC233551
0.5345	Remote Similarity	NPC40376
0.5345	Remote Similarity	NPC21208
0.5263	Remote Similarity	NPC473707
0.5263	Remote Similarity	NPC20339

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC202055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6224
0.1-0.2	2841
0.2-0.3	84
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