NPASS Compound

Natural Product: NPC488245

Natural Product ID	NPC488245
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BXVOYQPIMROCGF-HNZHMDFNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10372038
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 116117 0 0 0 0 0 0 0 0999 V2000 13.9513 2.6825 0.8621 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5631 3.2524 0.9648 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6440 2.3442 0.1484 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7382 0.9723 0.7599 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8712 -0.0495 0.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4363 0.3803 0.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5046 -0.6249 -0.5802 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5856 -1.9585 0.0405 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7134 -3.0125 -0.4770 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2806 -2.9340 -0.2221 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5316 -1.7347 -0.6587 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0197 -1.8910 -0.3949 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4025 -3.0058 -1.1104 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4078 -2.9006 -1.9848 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7816 -1.6350 -2.3567 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3187 -1.5114 -2.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1649 -1.6972 -0.7318 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4012 -0.7804 0.3128 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3101 0.6507 0.1070 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0697 1.2775 0.0090 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8151 2.7348 -0.2265 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9729 3.6293 -0.3314 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8515 3.8660 0.8054 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6408 2.8203 1.4582 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6506 2.1119 0.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2498 1.1732 1.2056 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0166 2.4194 -0.7304 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4343 1.9320 -1.0966 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4286 2.6170 -0.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8426 2.2848 -0.4781 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1903 0.8527 -0.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9149 0.2880 0.9802 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3282 -1.1748 1.0027 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7839 -1.2475 0.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3462 -1.8577 -0.3248 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8056 -1.6892 -0.2473 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.2616 -0.8703 -1.4546 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0339 -0.9478 0.9476 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8190 -0.6644 1.5253 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7024 -0.0105 2.5826 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4320 1.0176 2.0287 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2958 -1.3049 1.4237 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2777 -2.6938 1.2128 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6252 -3.3276 1.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7562 -3.2768 2.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0656 -2.9135 -0.1298 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7383 3.4595 0.9790 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0892 1.9746 1.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0754 2.1317 -0.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2302 3.2157 2.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5288 4.2929 0.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9292 2.3585 -0.9067 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5963 2.7222 0.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4200 1.0266 1.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7853 0.6144 0.7056 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1910 -0.0753 -1.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0673 -1.0562 0.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2767 1.3587 -0.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1091 0.4384 1.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9603 -0.7017 -1.6476 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5681 -0.1159 -0.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4714 -1.8085 1.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6612 -2.3638 -0.0086 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8712 -3.1112 -1.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0635 -4.0358 -0.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1213 -3.0766 0.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7281 -3.8415 -0.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8530 -0.9050 0.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7417 -1.3529 -1.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5780 -0.9081 -0.5063 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9873 -2.0984 0.7225 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7634 -4.0344 -0.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0456 -3.8096 -2.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2615 -0.7400 -1.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9099 -1.4353 -3.4810 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2455 -2.2526 -2.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0643 -0.5271 -2.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2854 -1.5499 -0.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4687 -1.0309 0.5518 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8624 1.1813 0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8190 0.9129 -0.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5776 0.9013 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6454 1.0689 0.8876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1033 2.8718 -1.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1656 3.1587 0.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 3.3140 -1.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5194 4.6588 -0.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5238 4.7846 0.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2068 4.3547 1.6341 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2696 3.4262 2.2568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0882 2.1400 2.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3152 1.8435 -1.3968 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9321 3.5002 -0.9232 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6284 2.2135 -2.1508 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4737 0.8374 -1.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3204 3.7456 -0.2930 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1390 2.4046 0.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0435 2.5994 -1.5447 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4991 2.9376 0.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5839 0.2924 -1.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2495 0.6506 -0.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8001 0.2865 1.1249 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0658 -1.6360 1.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7749 -1.6897 0.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8136 -2.3875 -1.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3516 -2.6570 -0.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0167 -1.4388 -2.3682 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7001 0.0738 -1.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3624 -0.6816 -1.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8624 0.9520 2.8529 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9274 -3.9751 0.5529 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6021 -4.0615 2.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4496 -2.6105 1.5632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6884 -3.5520 1.6143 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0305 -2.5951 2.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3227 -4.1806 2.6194 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 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 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 2 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 2 0 32 41 1 0 18 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 43 46 1 0 46 17 1 0 39 34 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 8 62 1 0 8 63 1 0 9 64 1 0 9 65 1 0 10 66 1 0 10 67 1 0 11 68 1 0 11 69 1 0 12 70 1 0 12 71 1 0 13 72 1 0 14 73 1 0 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 6 18 79 1 1 19 80 1 0 19 81 1 0 20 82 1 0 20 83 1 0 21 84 1 0 21 85 1 0 22 86 1 0 22 87 1 0 23 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 27 92 1 0 27 93 1 0 28 94 1 0 28 95 1 0 29 96 1 0 29 97 1 0 30 98 1 0 30 99 1 0 31100 1 0 31101 1 0 32102 1 1 33103 1 0 33104 1 0 35105 1 0 36106 1 1 37107 1 0 37108 1 0 37109 1 0 41110 1 0 44111 1 0 44112 1 0 44113 1 0 45114 1 0 45115 1 0 45116 1 0 M END

Standard InCHIKey	BXVOYQPIMROCGF-HNZHMDFNSA-N
Standard InCHI	InChI=1S/C40H70O6/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-24-29-37-38(46-40(3,4)45-37)30-25-19-18-21-26-35(41)27-22-20-23-28-36(42)32-34-31-33(2)44-39(34)43/h16-17,31,33,36-38,42H,5-15,18-30,32H2,1-4H3/b17-16-/t33-,36+,37+,38+/m0/s1
SMILES	CCCCCCCCCCCC/C=CCC[C@@H]1[C@@H](CCCCCCC(=O)CCCCC[C@H](CC2=C[C@H](C)OC2=O)O)OC(C)(C)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	646.52	Volume:	725.478 ? Van der Waals volume.
Dense:	0.891	LogP:	7.683 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.682 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.978 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	29.0	Rigid Bonds:	13.0
TPSA:	82.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.379	Fsp³:	0.85
MCE-18:	33.73 ? 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:	0.632	Fluc inhibitor:	0.037 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.009 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.578	Promiscuous compounds:	0.468

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.119	MDCK Permeability:	-4.732
Pgp-inhibitor:	0.166	Pgp-substrate:	0.007
PAMPA:	0.0 ? 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):	0.001
20% Bioavailability (F20%):	0.602	30% Bioavailability (F30%):	0.962
50% Bioavailability (F50%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	98.17%	Volume Distribution (VD):	0.108
Fu:	0.819% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.098
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.896
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.705
CYP2C9-inhibitor:	0.289	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.515 ? 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):

5.32

Half-life (T1/2):

1.119

ADMET: Toxicity

hERG Blockers:	0.476	hERG Blockers (10um):	0.869
Human Hepatotoxicity (H-HT):	0.577	Drug-induced Liver Injury (DILI):	0.112
AMES Toxicity:	0.471	Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.808	Skin Sensitization:	1.0
Carcinogencity:	0.492	Eye Corrosion:	0.268
Eye Irritation:	0.8	Respiratory Toxicity:	0.882
Drug-induced Neurotoxicity:	0.029	Ototoxicity:	0.404
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.813
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.946	Hek293 Cytotoxicity:	0.636
BCF:	0.399 ? 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:	4.656 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.483 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.168 ? 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
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[7623031]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[7714532]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[8021648]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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	3

Activity Type	# Activity
Cell line	3

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	<	1.0	10'-3 ug/ml	PMID[7623031]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	3.47	10'-1 ug/ml	PMID[7623031]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	9.32	10'-1 ug/ml	PMID[7623031]

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 NPC488245 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	18515
0.1-0.2	28857
0.2-0.3	2158
0.3-0.4	144
0.4-0.5	105
0.5-0.6	54
0.6-0.7	12
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
0.7288	Intermediate Similarity	NPC488244
0.6613	Remote Similarity	NPC488623
0.6613	Remote Similarity	NPC488624
0.6613	Remote Similarity	NPC488629
0.623	Remote Similarity	NPC473687
0.623	Remote Similarity	NPC204686
0.623	Remote Similarity	NPC219498
0.623	Remote Similarity	NPC308412
0.623	Remote Similarity	NPC134885
0.623	Remote Similarity	NPC488247
0.623	Remote Similarity	NPC210218
0.623	Remote Similarity	NPC488248
0.6167	Remote Similarity	NPC488246
0.5873	Remote Similarity	NPC134807
0.5873	Remote Similarity	NPC488250
0.5873	Remote Similarity	NPC600188
0.5818	Remote Similarity	NPC608138
0.5781	Remote Similarity	NPC69082
0.5781	Remote Similarity	NPC488249
0.5645	Remote Similarity	NPC480080
0.5441	Remote Similarity	NPC488630
0.5441	Remote Similarity	NPC488625
0.5441	Remote Similarity	NPC488626
0.5352	Remote Similarity	NPC482766
0.5303	Remote Similarity	NPC473707
0.5246	Remote Similarity	NPC606043
0.5238	Remote Similarity	NPC81045
0.5238	Remote Similarity	NPC39754
0.5238	Remote Similarity	NPC171135
0.5238	Remote Similarity	NPC182383
0.5238	Remote Similarity	NPC61257
0.5238	Remote Similarity	NPC320569
0.5238	Remote Similarity	NPC133730
0.5238	Remote Similarity	NPC191929
0.5238	Remote Similarity	NPC100454
0.5238	Remote Similarity	NPC242364
0.5238	Remote Similarity	NPC172821
0.5238	Remote Similarity	NPC274446
0.5238	Remote Similarity	NPC485251
0.5238	Remote Similarity	NPC151403
0.5238	Remote Similarity	NPC261952
0.5238	Remote Similarity	NPC605171
0.5224	Remote Similarity	NPC130359
0.5224	Remote Similarity	NPC14901
0.5217	Remote Similarity	NPC480081
0.5161	Remote Similarity	NPC107986
0.5161	Remote Similarity	NPC223871
0.5161	Remote Similarity	NPC231009
0.5161	Remote Similarity	NPC103284
0.5161	Remote Similarity	NPC110710
0.5161	Remote Similarity	NPC1083
0.5161	Remote Similarity	NPC82795
0.5161	Remote Similarity	NPC286338
0.5161	Remote Similarity	NPC603931
0.5161	Remote Similarity	NPC604237
0.5156	Remote Similarity	NPC93794
0.5156	Remote Similarity	NPC473504
0.5156	Remote Similarity	NPC81778
0.5156	Remote Similarity	NPC40066
0.5156	Remote Similarity	NPC47937
0.5152	Remote Similarity	NPC477010
0.5152	Remote Similarity	NPC602738
0.5082	Remote Similarity	NPC112685
0.5079	Remote Similarity	NPC488253
0.5079	Remote Similarity	NPC473669
0.5079	Remote Similarity	NPC488251
0.5077	Remote Similarity	NPC480079

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488245 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6691
0.1-0.2	2395
0.2-0.3	62
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