NPASS Compound

Natural Product: NPC105638

Natural Product ID	NPC105638
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VZEPVAAWZDUQLP-FYHSANBVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9986398
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 110112 0 0 0 0 0 0 0 0999 V2000 -11.9703 -4.2174 1.7446 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5383 -4.6076 2.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6669 -4.5185 0.8224 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6119 -3.1547 0.2354 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0604 -2.1113 1.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0368 -0.7633 0.5375 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5064 0.3445 1.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0924 0.1874 1.8365 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1283 0.0702 0.6553 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1939 1.2598 -0.2282 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3216 1.1575 -1.4245 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8444 0.9957 -1.1797 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4653 -0.4619 -1.0078 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9947 -0.4033 -1.4316 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 0.6529 -2.4790 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9743 1.7104 -2.3456 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3978 1.1016 -2.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4566 2.1576 -2.2133 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3851 2.9966 -0.9844 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5143 2.2596 0.3050 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5039 3.2752 1.4342 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9402 3.7028 1.4758 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6635 2.5865 0.8047 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6353 1.9736 1.7848 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6486 2.8941 2.2997 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5695 3.6468 1.4657 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5710 3.0869 0.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3193 2.3112 -0.6339 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6388 1.0217 -0.6706 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2585 -0.0799 0.1816 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6454 -0.3340 -0.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4624 -1.3333 0.4358 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9681 -2.7067 0.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6028 -3.7491 -0.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8593 -4.9993 0.1941 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3646 -5.5787 -1.1147 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7752 -4.6616 1.0058 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8197 -3.2698 1.1814 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9556 -2.6299 1.8476 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7357 1.6188 0.4659 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3712 3.9736 -1.0641 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0665 2.6333 -3.3962 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2578 1.2574 -2.4446 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7155 0.1531 -2.3275 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.6791 -5.0747 1.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1005 -3.8736 0.6929 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3053 -3.4409 2.4762 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5597 -5.6850 2.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1261 -4.0567 2.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7014 -4.9644 1.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1487 -5.1836 0.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9021 -3.1967 -0.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5742 -2.8351 -0.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0709 -2.3487 1.5614 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7707 -2.0764 2.0537 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4787 -0.8657 -0.4296 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0704 -0.4505 0.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6763 1.2954 0.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1388 0.4095 2.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9944 -0.7195 2.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8081 1.0513 2.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1657 -0.8745 0.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1150 0.1269 1.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9224 2.2013 0.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2310 1.4736 -0.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4621 2.1075 -2.0717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4418 1.6332 -0.3892 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4825 -0.8441 0.0032 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0165 -1.1051 -1.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6406 -1.3911 -1.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4247 -0.0650 -0.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9645 0.1396 -3.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1952 2.2842 -1.4196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5068 0.2831 -1.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5437 0.6380 -3.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4613 1.7148 -2.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2992 2.8582 -3.0860 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3677 3.4877 -0.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7109 1.5437 0.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8036 4.0909 1.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2565 2.7139 2.3633 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1199 4.7061 1.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2254 3.8195 2.5532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1856 2.8803 -0.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9344 1.7788 2.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9092 0.9554 1.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1789 3.5900 3.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3078 2.2537 3.0063 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1923 4.2868 2.2211 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0235 4.5347 0.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1898 4.0110 0.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3976 2.6022 1.2151 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7374 3.0154 -1.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2962 2.2232 -1.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5484 0.9778 -0.6643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8580 0.6095 -1.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1014 0.0365 1.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6581 -0.9956 -0.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6335 -0.6510 -1.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2099 0.6493 -0.3401 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6711 -0.9782 1.4996 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4983 -1.3008 -0.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5165 -3.6985 -0.6087 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5452 -5.7213 0.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4940 -4.8669 -1.9539 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2864 -5.7954 -1.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8851 -6.5325 -1.3488 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5307 4.1562 -2.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9463 2.5946 -3.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5575 0.4094 -2.7796 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 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 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 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 23 40 1 0 19 41 1 0 16 42 1 0 15 43 1 0 11 44 1 0 43 12 1 0 40 20 1 0 38 33 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 6 12 67 1 1 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 6 16 73 1 1 17 74 1 0 17 75 1 0 18 76 1 0 18 77 1 0 19 78 1 1 20 79 1 1 21 80 1 0 21 81 1 0 22 82 1 0 22 83 1 0 23 84 1 6 24 85 1 0 24 86 1 0 25 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 32101 1 0 32102 1 0 34103 1 0 35104 1 1 36105 1 0 36106 1 0 36107 1 0 41108 1 0 42109 1 0 44110 1 0 M END

Standard InCHIKey	VZEPVAAWZDUQLP-FYHSANBVSA-N
Standard InCHI	InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(38)35-25-26-36(44-35)33(40)23-22-32(39)34-24-21-30(43-34)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30+,31-,32-,33+,34-,35+,36+/m0/s1
SMILES	CCCCCCCCCC[C@@H]([C@H]1CC[C@H]([C@@H](CC[C@@H]([C@@H]2CC[C@@H](CCCCCCCCCC3=C[C@H](C)OC3=O)O2)O)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.48	Volume:	679.097 ? Van der Waals volume.
Dense:	0.917	LogP:	5.635 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.077 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.925 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	105.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.07	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.835	Fsp³:	0.919
MCE-18:	42.817 ? 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:	0.884	Fluc inhibitor:	0.046 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.079 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.581	Promiscuous compounds:	0.363

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.141	MDCK Permeability:	-4.841
Pgp-inhibitor:	0.004	Pgp-substrate:	0.806
PAMPA:	0.011 ? 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):	0.09
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.971
Plasma Protein Binding (PPB):	98.191%	Volume Distribution (VD):	0.821
Fu:	1.814% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.932
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.772
BSEP inhibitor:	0.529

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.897	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.472
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.037 ? 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):

4.984

Half-life (T1/2):

1.135

ADMET: Toxicity

hERG Blockers:	0.584	hERG Blockers (10um):	0.864
Human Hepatotoxicity (H-HT):	0.719	Drug-induced Liver Injury (DILI):	0.388
AMES Toxicity:	0.593	Rat Oral Acute Toxicity:	0.348
Maximum Recommended Daily Dose:	0.92	Skin Sensitization:	1.0
Carcinogencity:	0.385	Eye Corrosion:	0.103
Eye Irritation:	0.706	Respiratory Toxicity:	0.97
Drug-induced Neurotoxicity:	0.18	Ototoxicity:	0.502
Hematotoxicity:	0.222	Drug-induced Nephrotoxicity:	0.896
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.546
BCF:	0.877 ? 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:	4.899 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.351 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.789 ? 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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	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

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

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 NPC105638 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	16155
0.1-0.2	30106
0.2-0.3	3259
0.3-0.4	104
0.4-0.5	26
0.5-0.6	54
0.6-0.7	79
0.7-0.8	0
0.8-0.85	17
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC241360
1.0	High Similarity	NPC293136
0.9167	High Similarity	NPC258068
0.9167	High Similarity	NPC476583
0.8936	High Similarity	NPC65930
0.875	High Similarity	NPC329615
0.8409	Intermediate Similarity	NPC73310
0.8409	Intermediate Similarity	NPC473529
0.8409	Intermediate Similarity	NPC180363
0.8409	Intermediate Similarity	NPC94875
0.8409	Intermediate Similarity	NPC11332
0.8409	Intermediate Similarity	NPC145914
0.8409	Intermediate Similarity	NPC601174
0.8409	Intermediate Similarity	NPC601403
0.8409	Intermediate Similarity	NPC603568
0.8409	Intermediate Similarity	NPC604330
0.8409	Intermediate Similarity	NPC608300
0.8409	Intermediate Similarity	NPC611200
0.8409	Intermediate Similarity	NPC611571
0.8235	Intermediate Similarity	NPC320458
0.8	Intermediate Similarity	NPC20621
0.8	Intermediate Similarity	NPC318963
0.8	Intermediate Similarity	NPC605101
0.7917	Intermediate Similarity	NPC156804
0.7885	Intermediate Similarity	NPC480082
0.7872	Intermediate Similarity	NPC329829
0.7872	Intermediate Similarity	NPC475159
0.7872	Intermediate Similarity	NPC131002
0.7872	Intermediate Similarity	NPC473780
0.7872	Intermediate Similarity	NPC604521
0.7778	Intermediate Similarity	NPC253801
0.7692	Intermediate Similarity	NPC473995
0.7593	Intermediate Similarity	NPC473520
0.7593	Intermediate Similarity	NPC322529
0.7547	Intermediate Similarity	NPC477014
0.7547	Intermediate Similarity	NPC477013
0.75	Intermediate Similarity	NPC25764
0.75	Intermediate Similarity	NPC235809
0.75	Intermediate Similarity	NPC39279
0.75	Intermediate Similarity	NPC39167
0.75	Intermediate Similarity	NPC292809
0.75	Intermediate Similarity	NPC202055
0.75	Intermediate Similarity	NPC606804
0.75	Intermediate Similarity	NPC607425
0.75	Intermediate Similarity	NPC608574
0.74	Intermediate Similarity	NPC163093
0.74	Intermediate Similarity	NPC144415
0.74	Intermediate Similarity	NPC607439
0.74	Intermediate Similarity	NPC608157
0.7308	Intermediate Similarity	NPC329838
0.717	Intermediate Similarity	NPC473478
0.717	Intermediate Similarity	NPC473651
0.717	Intermediate Similarity	NPC66346
0.7143	Intermediate Similarity	NPC100921
0.7143	Intermediate Similarity	NPC477018
0.7143	Intermediate Similarity	NPC477015
0.7115	Intermediate Similarity	NPC132940
0.7059	Intermediate Similarity	NPC473156
0.7059	Intermediate Similarity	NPC282815
0.7059	Intermediate Similarity	NPC600956
0.7037	Intermediate Similarity	NPC231096
0.7037	Intermediate Similarity	NPC475581
0.7037	Intermediate Similarity	NPC283085
0.7037	Intermediate Similarity	NPC62118
0.7037	Intermediate Similarity	NPC132496
0.7037	Intermediate Similarity	NPC107717
0.7037	Intermediate Similarity	NPC488252
0.6981	Remote Similarity	NPC20533
0.6923	Remote Similarity	NPC473671
0.6923	Remote Similarity	NPC219652
0.6923	Remote Similarity	NPC475268
0.6923	Remote Similarity	NPC473840
0.6923	Remote Similarity	NPC470400
0.6923	Remote Similarity	NPC77871
0.6923	Remote Similarity	NPC9678
0.6923	Remote Similarity	NPC319036
0.6923	Remote Similarity	NPC605867
0.6731	Remote Similarity	NPC610454
0.6727	Remote Similarity	NPC169511
0.6727	Remote Similarity	NPC287164
0.6727	Remote Similarity	NPC234077
0.6727	Remote Similarity	NPC606740
0.6727	Remote Similarity	NPC608614
0.6667	Remote Similarity	NPC485250
0.6667	Remote Similarity	NPC605396
0.6604	Remote Similarity	NPC25703
0.66	Remote Similarity	NPC606043
0.6538	Remote Similarity	NPC232555
0.6538	Remote Similarity	NPC171174
0.6538	Remote Similarity	NPC114694
0.6538	Remote Similarity	NPC485248
0.6538	Remote Similarity	NPC142117
0.6538	Remote Similarity	NPC480249
0.6538	Remote Similarity	NPC485249
0.6538	Remote Similarity	NPC240695
0.6471	Remote Similarity	NPC107986
0.6471	Remote Similarity	NPC223871
0.6471	Remote Similarity	NPC231009
0.6471	Remote Similarity	NPC103284
0.6471	Remote Similarity	NPC110710
0.6471	Remote Similarity	NPC1083
0.6471	Remote Similarity	NPC82795
0.6471	Remote Similarity	NPC286338
0.6471	Remote Similarity	NPC603931
0.6471	Remote Similarity	NPC604237
0.6429	Remote Similarity	NPC120398
0.6429	Remote Similarity	NPC471567
0.6415	Remote Similarity	NPC488632
0.6415	Remote Similarity	NPC473649
0.6415	Remote Similarity	NPC154097
0.6415	Remote Similarity	NPC159750
0.6415	Remote Similarity	NPC73248
0.6415	Remote Similarity	NPC470401
0.6415	Remote Similarity	NPC600524
0.6415	Remote Similarity	NPC608355
0.6383	Remote Similarity	NPC609415
0.6379	Remote Similarity	NPC91067
0.6379	Remote Similarity	NPC480081
0.6364	Remote Similarity	NPC309211
0.6364	Remote Similarity	NPC477010
0.6346	Remote Similarity	NPC488253
0.6346	Remote Similarity	NPC473669
0.6346	Remote Similarity	NPC488251
0.6296	Remote Similarity	NPC280621
0.6296	Remote Similarity	NPC48338
0.6296	Remote Similarity	NPC488628
0.6296	Remote Similarity	NPC604764
0.625	Remote Similarity	NPC477012
0.623	Remote Similarity	NPC477017
0.623	Remote Similarity	NPC477016
0.6226	Remote Similarity	NPC182383
0.6111	Remote Similarity	NPC134865
0.6111	Remote Similarity	NPC103523
0.6111	Remote Similarity	NPC488627
0.6111	Remote Similarity	NPC47937
0.6111	Remote Similarity	NPC488631
0.6111	Remote Similarity	NPC477011
0.6102	Remote Similarity	NPC488630
0.6102	Remote Similarity	NPC488625
0.6102	Remote Similarity	NPC488626
0.6102	Remote Similarity	NPC280612
0.6034	Remote Similarity	NPC233551
0.6034	Remote Similarity	NPC40376
0.6034	Remote Similarity	NPC21208
0.6	Remote Similarity	NPC473905
0.6	Remote Similarity	NPC475616
0.5968	Remote Similarity	NPC482766
0.5968	Remote Similarity	NPC279267
0.5926	Remote Similarity	NPC81045
0.5926	Remote Similarity	NPC39754
0.5926	Remote Similarity	NPC171135
0.5926	Remote Similarity	NPC61257
0.5926	Remote Similarity	NPC320569
0.5926	Remote Similarity	NPC133730
0.5926	Remote Similarity	NPC191929
0.5926	Remote Similarity	NPC100454
0.5926	Remote Similarity	NPC242364
0.5926	Remote Similarity	NPC172821
0.5926	Remote Similarity	NPC274446
0.5926	Remote Similarity	NPC485251
0.5926	Remote Similarity	NPC151403
0.5926	Remote Similarity	NPC261952
0.5926	Remote Similarity	NPC605171
0.5902	Remote Similarity	NPC473663
0.5902	Remote Similarity	NPC473723
0.5902	Remote Similarity	NPC475173
0.5893	Remote Similarity	NPC178215
0.5893	Remote Similarity	NPC42598
0.5893	Remote Similarity	NPC473687
0.5893	Remote Similarity	NPC204686
0.5893	Remote Similarity	NPC219498
0.5893	Remote Similarity	NPC308412
0.5893	Remote Similarity	NPC134885
0.5893	Remote Similarity	NPC488247
0.5893	Remote Similarity	NPC210218
0.5893	Remote Similarity	NPC488248
0.5818	Remote Similarity	NPC93794
0.5818	Remote Similarity	NPC473504
0.5818	Remote Similarity	NPC81778
0.5818	Remote Similarity	NPC40066
0.5789	Remote Similarity	NPC134807
0.5789	Remote Similarity	NPC488250
0.5789	Remote Similarity	NPC602738
0.5763	Remote Similarity	NPC89001
0.5763	Remote Similarity	NPC488623
0.5763	Remote Similarity	NPC488624
0.5763	Remote Similarity	NPC488629
0.569	Remote Similarity	NPC69082
0.569	Remote Similarity	NPC488249
0.5593	Remote Similarity	NPC130359
0.5593	Remote Similarity	NPC14901
0.5424	Remote Similarity	NPC139418
0.5345	Remote Similarity	NPC478998
0.5273	Remote Similarity	NPC474100
0.5273	Remote Similarity	NPC475232
0.5227	Remote Similarity	NPC84038
0.5185	Remote Similarity	NPC112685
0.5167	Remote Similarity	NPC20339
0.5161	Remote Similarity	NPC239517
0.5098	Remote Similarity	NPC608138

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC105638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6361
0.1-0.2	2722
0.2-0.3	67
0.3-0.4	0
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