NPASS Compound

Natural Product: NPC167375

Natural Product ID	NPC167375
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZPRYGZNEAVBQEP-PJDABLFQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10817542
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 107108 0 0 0 0 0 0 0 0999 V2000 12.8209 -3.5498 -0.8567 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2251 -2.1643 -0.6975 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0367 -2.0344 -1.6318 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9993 -3.0775 -1.2824 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4797 -2.9875 0.0853 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8355 -1.7874 0.5969 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5845 -1.2557 0.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5472 -0.8368 -1.3898 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1634 -0.3063 -1.7426 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8349 0.8831 -0.9237 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4545 1.4832 -1.2574 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3443 0.5068 -1.0181 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9844 1.0697 -1.3377 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6402 2.2712 -0.5278 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1862 2.7166 -0.7901 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0790 3.9511 0.0602 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4067 4.5479 -0.0780 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6232 3.7899 0.2523 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9172 3.6254 1.7008 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4163 2.1704 1.7143 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8320 1.8934 0.3739 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9815 2.2189 -0.3902 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3902 1.9403 -0.1957 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1046 2.5048 0.9470 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7869 2.2424 2.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8713 0.8063 2.8191 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2882 0.3808 2.6395 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5302 -0.9882 3.1298 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7264 -2.0186 2.3989 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0713 -2.0018 0.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2751 -3.0571 0.2314 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3998 -2.8366 -0.7419 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8153 -4.1216 -1.1933 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1587 -4.3393 -2.6585 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4340 -5.1001 -0.4120 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3266 -4.4864 0.4693 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0227 -5.1481 1.3004 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9789 -3.2440 3.0217 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0679 2.5078 -1.3467 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7099 2.5449 -0.3313 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4038 5.7946 0.5934 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4067 3.4072 -0.8597 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7951 1.2732 -2.7052 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6279 -3.9480 -1.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4015 -4.2935 -0.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9281 -3.5426 -0.7295 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8862 -2.1101 0.3774 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0125 -1.4424 -0.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6461 -1.0240 -1.7173 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4219 -2.3246 -2.6532 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3277 -3.2170 -2.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6209 -4.0547 -1.2959 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3110 -3.2976 0.8090 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7488 -3.8511 0.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5863 -0.9300 0.7766 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5684 -2.0160 1.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2785 -0.3685 0.6576 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7079 -1.9599 0.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2329 0.0218 -1.5684 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7111 -1.6561 -2.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2161 0.0413 -2.8130 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3924 -1.1032 -1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5452 1.7256 -1.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8144 0.7140 0.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3877 2.3493 -0.5337 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5187 1.8261 -2.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3405 0.2378 0.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4729 -0.4408 -1.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2345 0.2719 -1.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7118 2.0772 0.5580 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0786 2.9886 -1.8429 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4328 1.8697 -0.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6646 4.7112 -0.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2665 3.7944 1.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5123 4.8615 -1.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4839 4.4319 -0.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0322 3.6995 2.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6839 4.3367 2.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9668 2.0038 2.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4389 1.5512 1.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5081 0.7924 0.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7233 1.8648 -1.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9615 3.3629 -0.6605 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6658 0.8461 -0.3766 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0659 3.6611 0.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2445 2.3681 0.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7019 2.7089 2.9242 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9781 2.8332 2.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6282 0.8321 3.8996 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1243 0.1599 2.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5850 0.5269 1.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9106 1.1042 3.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3611 -1.0724 4.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6337 -1.2334 2.9971 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6336 -1.7857 2.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8810 -1.0298 0.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1616 -2.2001 0.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1587 -1.8745 -1.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7034 -4.1528 -1.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2336 -4.1815 -2.8564 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9397 -5.4046 -2.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5759 -3.6918 -3.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7130 -3.1236 3.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4655 2.4797 -2.1309 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4718 6.0853 0.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3929 3.5012 -1.8448 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8052 0.4571 -3.2263 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 2 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 2 0 29 38 1 0 23 39 1 0 21 40 1 0 17 41 1 0 14 42 1 0 13 43 1 0 40 18 1 0 36 31 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 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 0 14 70 1 0 15 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 6 18 76 1 6 19 77 1 0 19 78 1 0 20 79 1 0 20 80 1 0 21 81 1 1 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 6 30 96 1 0 30 97 1 0 32 98 1 0 33 99 1 6 34100 1 0 34101 1 0 34102 1 0 38103 1 0 39104 1 0 41105 1 0 42106 1 0 43107 1 0 M END

Standard InCHIKey	ZPRYGZNEAVBQEP-PJDABLFQSA-N
Standard InCHI	InChI=1S/C35H64O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(38)32(39)20-21-33(40)34-22-19-30(43-34)25-29(37)17-14-12-13-16-28(36)24-27-23-26(2)42-35(27)41/h23,26,28-34,36-40H,3-22,24-25H2,1-2H3/t26-,28+,29+,30-,31?,32?,33-,34-/m0/s1
SMILES	CCCCCCCCCCCCC(C(CC[C@@H]([C@@H]1CC[C@@H](C[C@@H](CCCCC[C@H](CC2=C[C@H](C)OC2=O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	612.46	Volume:	661.852 ? Van der Waals volume.
Dense:	0.925	LogP:	4.073 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.204 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.138 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	Rigid Bonds:	11.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.059	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.796	Fsp³:	0.914
MCE-18:	34.388 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.806	Fluc inhibitor:	0.014 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.092 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.478	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.214	MDCK Permeability:	-4.859
Pgp-inhibitor:	0.0	Pgp-substrate:	0.988
PAMPA:	0.296 ? 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):	0.11
20% Bioavailability (F20%):	0.981	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.942
Plasma Protein Binding (PPB):	92.995%	Volume Distribution (VD):	0.353
Fu:	5.797% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.125
OATP1B3 inhibitor:	0.966	BCRP inhibitor:	0.659
BSEP inhibitor:	0.362

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.218
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.622
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):

6.565

Half-life (T1/2):

1.043

ADMET: Toxicity

hERG Blockers:	0.491	hERG Blockers (10um):	0.831
Human Hepatotoxicity (H-HT):	0.672	Drug-induced Liver Injury (DILI):	0.278
AMES Toxicity:	0.234	Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.985	Skin Sensitization:	0.999
Carcinogencity:	0.456	Eye Corrosion:	0.0
Eye Irritation:	0.214	Respiratory Toxicity:	0.947
Drug-induced Neurotoxicity:	0.197	Ototoxicity:	0.955
Hematotoxicity:	0.078	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.987	Hek293 Cytotoxicity:	0.57
BCF:	1.479 ? 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:	5.009 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.147 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.354 ? 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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	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 NPC167375 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	18532
0.1-0.2	29167
0.2-0.3	1868
0.3-0.4	64
0.4-0.5	31
0.5-0.6	77
0.6-0.7	74
0.7-0.8	0
0.8-0.85	5
0.85-0.9	5
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233551
1.0	High Similarity	NPC40376
1.0	High Similarity	NPC21208
0.8654	High Similarity	NPC231096
0.8654	High Similarity	NPC475581
0.8654	High Similarity	NPC62118
0.8654	High Similarity	NPC107717
0.8654	High Similarity	NPC488252
0.8302	Intermediate Similarity	NPC606740
0.8302	Intermediate Similarity	NPC608614
0.8113	Intermediate Similarity	NPC473478
0.8113	Intermediate Similarity	NPC473651
0.8113	Intermediate Similarity	NPC66346
0.7963	Intermediate Similarity	NPC283085
0.7963	Intermediate Similarity	NPC132496
0.7692	Intermediate Similarity	NPC134865
0.7692	Intermediate Similarity	NPC103523
0.7692	Intermediate Similarity	NPC488627
0.7692	Intermediate Similarity	NPC488631
0.7593	Intermediate Similarity	NPC20621
0.7593	Intermediate Similarity	NPC318963
0.7593	Intermediate Similarity	NPC605101
0.7544	Intermediate Similarity	NPC480081
0.7255	Intermediate Similarity	NPC606043
0.7241	Intermediate Similarity	NPC91067
0.717	Intermediate Similarity	NPC232555
0.717	Intermediate Similarity	NPC171174
0.717	Intermediate Similarity	NPC114694
0.717	Intermediate Similarity	NPC485248
0.717	Intermediate Similarity	NPC142117
0.717	Intermediate Similarity	NPC480249
0.717	Intermediate Similarity	NPC485249
0.717	Intermediate Similarity	NPC240695
0.7115	Intermediate Similarity	NPC107986
0.7115	Intermediate Similarity	NPC223871
0.7115	Intermediate Similarity	NPC231009
0.7115	Intermediate Similarity	NPC103284
0.7115	Intermediate Similarity	NPC110710
0.7115	Intermediate Similarity	NPC1083
0.7115	Intermediate Similarity	NPC82795
0.7115	Intermediate Similarity	NPC286338
0.7115	Intermediate Similarity	NPC603931
0.7115	Intermediate Similarity	NPC604237
0.7049	Intermediate Similarity	NPC279267
0.7037	Intermediate Similarity	NPC488632
0.7037	Intermediate Similarity	NPC477011
0.6981	Remote Similarity	NPC488253
0.6981	Remote Similarity	NPC473669
0.6981	Remote Similarity	NPC488251
0.6964	Remote Similarity	NPC329615
0.6909	Remote Similarity	NPC280621
0.6909	Remote Similarity	NPC48338
0.6909	Remote Similarity	NPC488628
0.6852	Remote Similarity	NPC81045
0.6852	Remote Similarity	NPC39754
0.6852	Remote Similarity	NPC171135
0.6852	Remote Similarity	NPC61257
0.6852	Remote Similarity	NPC320569
0.6852	Remote Similarity	NPC133730
0.6852	Remote Similarity	NPC191929
0.6852	Remote Similarity	NPC100454
0.6852	Remote Similarity	NPC242364
0.6852	Remote Similarity	NPC172821
0.6852	Remote Similarity	NPC274446
0.6852	Remote Similarity	NPC485251
0.6852	Remote Similarity	NPC151403
0.6852	Remote Similarity	NPC261952
0.6852	Remote Similarity	NPC605171
0.6786	Remote Similarity	NPC178215
0.6786	Remote Similarity	NPC42598
0.6727	Remote Similarity	NPC93794
0.6727	Remote Similarity	NPC473504
0.6727	Remote Similarity	NPC81778
0.6727	Remote Similarity	NPC40066
0.6727	Remote Similarity	NPC47937
0.6724	Remote Similarity	NPC169511
0.6724	Remote Similarity	NPC287164
0.6724	Remote Similarity	NPC234077
0.6667	Remote Similarity	NPC329838
0.6545	Remote Similarity	NPC182383
0.6508	Remote Similarity	NPC482766
0.6491	Remote Similarity	NPC473687
0.6491	Remote Similarity	NPC204686
0.6491	Remote Similarity	NPC219498
0.6491	Remote Similarity	NPC65930
0.6491	Remote Similarity	NPC308412
0.6491	Remote Similarity	NPC134885
0.6491	Remote Similarity	NPC488247
0.6491	Remote Similarity	NPC210218
0.6491	Remote Similarity	NPC488248
0.64	Remote Similarity	NPC608138
0.6379	Remote Similarity	NPC488250
0.6379	Remote Similarity	NPC602738
0.6316	Remote Similarity	NPC480079
0.6271	Remote Similarity	NPC69082
0.6271	Remote Similarity	NPC488249
0.6271	Remote Similarity	NPC20339
0.623	Remote Similarity	NPC239517
0.6207	Remote Similarity	NPC473904
0.619	Remote Similarity	NPC473663
0.619	Remote Similarity	NPC473723
0.619	Remote Similarity	NPC475173
0.6182	Remote Similarity	NPC329829
0.6167	Remote Similarity	NPC258068
0.6167	Remote Similarity	NPC130359
0.6167	Remote Similarity	NPC14901
0.6167	Remote Similarity	NPC476583
0.614	Remote Similarity	NPC488246
0.614	Remote Similarity	NPC480080
0.6129	Remote Similarity	NPC488630
0.6129	Remote Similarity	NPC488625
0.6129	Remote Similarity	NPC488626
0.6111	Remote Similarity	NPC112685
0.6102	Remote Similarity	NPC134807
0.6066	Remote Similarity	NPC488623
0.6066	Remote Similarity	NPC488624
0.6066	Remote Similarity	NPC480082
0.6066	Remote Similarity	NPC488629
0.6034	Remote Similarity	NPC241360
0.6034	Remote Similarity	NPC293136
0.5965	Remote Similarity	NPC156804
0.5893	Remote Similarity	NPC100921
0.5893	Remote Similarity	NPC475159
0.5893	Remote Similarity	NPC131002
0.5893	Remote Similarity	NPC473780
0.5893	Remote Similarity	NPC477018
0.5893	Remote Similarity	NPC604521
0.5873	Remote Similarity	NPC322529
0.5862	Remote Similarity	NPC163093
0.5862	Remote Similarity	NPC600524
0.5862	Remote Similarity	NPC608355
0.5806	Remote Similarity	NPC320458
0.5806	Remote Similarity	NPC477014
0.5806	Remote Similarity	NPC477013
0.5781	Remote Similarity	NPC253801
0.5763	Remote Similarity	NPC219652
0.5763	Remote Similarity	NPC473840
0.5667	Remote Similarity	NPC132940
0.5645	Remote Similarity	NPC120398
0.5645	Remote Similarity	NPC471567
0.5645	Remote Similarity	NPC488244
0.5636	Remote Similarity	NPC73310
0.5636	Remote Similarity	NPC473529
0.5636	Remote Similarity	NPC180363
0.5636	Remote Similarity	NPC94875
0.5636	Remote Similarity	NPC11332
0.5636	Remote Similarity	NPC145914
0.5636	Remote Similarity	NPC601174
0.5636	Remote Similarity	NPC601403
0.5636	Remote Similarity	NPC603568
0.5636	Remote Similarity	NPC604330
0.5636	Remote Similarity	NPC608300
0.5636	Remote Similarity	NPC611200
0.5636	Remote Similarity	NPC611571
0.5593	Remote Similarity	NPC473649
0.5593	Remote Similarity	NPC473156
0.5593	Remote Similarity	NPC154097
0.5593	Remote Similarity	NPC159750
0.5593	Remote Similarity	NPC73248
0.5593	Remote Similarity	NPC282815
0.5593	Remote Similarity	NPC470401
0.5593	Remote Similarity	NPC600956
0.5593	Remote Similarity	NPC610454
0.5574	Remote Similarity	NPC20533
0.5556	Remote Similarity	NPC89001
0.55	Remote Similarity	NPC473671
0.55	Remote Similarity	NPC475268
0.55	Remote Similarity	NPC470400
0.55	Remote Similarity	NPC25703
0.55	Remote Similarity	NPC77871
0.55	Remote Similarity	NPC9678
0.55	Remote Similarity	NPC319036
0.55	Remote Similarity	NPC604764
0.55	Remote Similarity	NPC605867
0.5484	Remote Similarity	NPC473707
0.5484	Remote Similarity	NPC477012
0.5472	Remote Similarity	NPC609415
0.5345	Remote Similarity	NPC25764
0.5345	Remote Similarity	NPC235809
0.5345	Remote Similarity	NPC39279
0.5345	Remote Similarity	NPC39167
0.5345	Remote Similarity	NPC292809
0.5345	Remote Similarity	NPC202055
0.5345	Remote Similarity	NPC606804
0.5345	Remote Similarity	NPC607425
0.5345	Remote Similarity	NPC608574
0.5323	Remote Similarity	NPC309211
0.5323	Remote Similarity	NPC485250
0.5323	Remote Similarity	NPC477010
0.5303	Remote Similarity	NPC473905
0.5294	Remote Similarity	NPC477017
0.5294	Remote Similarity	NPC477016
0.5152	Remote Similarity	NPC280612
0.5082	Remote Similarity	NPC144415
0.5082	Remote Similarity	NPC607439
0.5082	Remote Similarity	NPC608157
0.5075	Remote Similarity	NPC477015

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC167375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6682
0.1-0.2	2436
0.2-0.3	32
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