NPASS Compound

Natural Product: NPC488252

Natural Product ID	NPC488252
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VFRBLIGIRLWBKM-JBSVHPCSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11114652
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 106107 0 0 0 0 0 0 0 0999 V2000 13.4158 1.0575 2.2794 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9268 1.1824 2.0868 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4541 0.0655 1.1689 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1484 0.1726 -0.1462 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8817 1.4622 -0.8381 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4228 1.6565 -1.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9112 0.5708 -2.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4663 0.7733 -2.4134 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5330 0.7425 -1.2400 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5477 -0.5787 -0.5171 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6003 -0.5662 0.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1591 -0.2920 0.2108 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6690 -1.3258 -0.7375 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3064 -1.0900 -1.2205 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2092 -1.1138 -0.1906 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9366 -0.8458 -0.9755 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3367 -1.1439 -0.2695 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5991 -0.3692 0.9737 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9392 -0.7466 1.6102 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0292 -0.4634 0.6530 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2434 1.0049 0.3447 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5100 0.8620 -0.5148 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1854 -0.2892 0.1966 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5292 -1.3340 -0.8124 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2180 -2.5351 -0.2200 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5258 -2.1757 0.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4736 -1.5597 -0.5337 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8237 -1.1842 0.0779 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6941 -0.1922 1.1673 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9360 0.2148 1.8467 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0159 0.8213 1.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3939 2.1033 1.2561 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4843 2.4182 0.3353 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.6722 3.0254 1.0573 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7986 1.2231 -0.3060 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8830 0.2244 0.0820 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9468 -0.9150 -0.4207 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8962 0.9080 0.7981 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2994 -0.7836 1.1489 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9119 -2.0865 1.9068 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9335 0.4579 -1.4873 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3137 -0.2146 0.8263 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9067 1.7551 1.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6931 -0.0073 2.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7107 1.3377 3.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6650 2.1408 1.6457 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4012 1.0913 3.0729 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3611 0.1779 1.0871 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6648 -0.9190 1.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2640 0.0668 -0.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8299 -0.6689 -0.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4382 1.4542 -1.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2747 2.3414 -0.2640 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2613 2.6642 -1.6027 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8413 1.6317 -0.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5248 0.5207 -2.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9907 -0.4115 -1.5486 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1542 0.0571 -3.2171 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3775 1.7992 -2.8619 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5197 0.9898 -1.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8419 1.5359 -0.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3617 -1.4265 -1.2098 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5630 -0.7418 -0.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8899 0.2239 1.3486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5919 -1.5227 1.1836 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5818 -0.2989 1.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0656 0.7190 -0.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3793 -1.4671 -1.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6991 -2.3438 -0.2322 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0312 -1.8429 -2.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1998 -0.0718 -1.7224 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0643 -2.1646 0.2089 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0426 -1.5167 -1.8995 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1439 -1.0129 -1.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3301 -2.2596 -0.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7520 0.7124 0.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1943 -0.4669 1.7120 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0256 -0.1146 2.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9316 -1.0497 -0.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4293 1.4800 -0.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5790 1.5342 1.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1436 0.5663 -1.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1080 1.7848 -0.5178 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1038 0.1391 0.6693 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0848 -0.8848 -1.6461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5769 -1.7170 -1.2555 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5379 -3.0827 0.4586 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4672 -3.2211 -1.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3868 -1.5630 1.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9726 -3.1490 0.7844 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9830 -0.6597 -0.9715 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6851 -2.2297 -1.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4467 -0.8120 -0.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2822 -2.1079 0.4499 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0529 -0.6993 1.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7055 0.8771 2.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3482 -0.7149 2.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9726 2.8009 1.9689 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1183 3.1691 -0.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.6362 2.6238 0.6483 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6203 2.7896 2.1415 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6523 4.1098 0.9432 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1532 1.2215 -0.1063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3729 -2.6089 1.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2911 1.0460 -0.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4359 -0.7456 1.6847 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 19 40 1 0 16 41 1 0 15 42 1 0 39 20 1 0 36 31 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 1 16 73 1 6 17 74 1 0 17 75 1 0 18 76 1 0 18 77 1 0 19 78 1 1 20 79 1 6 21 80 1 0 21 81 1 0 22 82 1 0 22 83 1 0 23 84 1 1 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 1 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 40104 1 0 41105 1 0 42106 1 0 M END

Standard InCHIKey	VFRBLIGIRLWBKM-JBSVHPCSSA-N
Standard InCHI	InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-12-13-17-20-31(37)32(38)22-23-33(39)34-24-21-30(42-34)19-16-14-15-18-29(36)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33-,34-/m0/s1
SMILES	CCCCCCCCCCCCCC[C@H]([C@@H](CC[C@@H]([C@@H]1CC[C@@H](CCCCC[C@H](CC2=C[C@H](C)OC2=O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.47	Volume:	653.062 ? Van der Waals volume.
Dense:	0.913	LogP:	5.43 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.811 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.086 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	Rigid Bonds:	11.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.062	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.603	Fsp³:	0.914
MCE-18:	32.239 ? 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:	0.865	Fluc inhibitor:	0.057 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.076 ? 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:	0.574	Promiscuous compounds:	0.283

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.125	MDCK Permeability:	-4.872
Pgp-inhibitor:	0.0	Pgp-substrate:	0.805
PAMPA:	0.073 ? 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):	0.005
20% Bioavailability (F20%):	0.933	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.92
Plasma Protein Binding (PPB):	97.233%	Volume Distribution (VD):	0.493
Fu:	3.352% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.728
BSEP inhibitor:	0.227

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.111	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.985
HLM stability:	0.001 ? 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):

5.425

Half-life (T1/2):

1.077

ADMET: Toxicity

hERG Blockers:	0.506	hERG Blockers (10um):	0.83
Human Hepatotoxicity (H-HT):	0.621	Drug-induced Liver Injury (DILI):	0.499
AMES Toxicity:	0.409	Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.92	Skin Sensitization:	1.0
Carcinogencity:	0.398	Eye Corrosion:	0.044
Eye Irritation:	0.775	Respiratory Toxicity:	0.942
Drug-induced Neurotoxicity:	0.096	Ototoxicity:	0.628
Hematotoxicity:	0.18	Drug-induced Nephrotoxicity:	0.928
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.479
BCF:	1.21 ? 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:	4.968 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.171 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.799 ? 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
IC50	1
Activity	1
ED50	6
Ratio	2

Activity Type	# Activity
Cell line	7
Others	1
Organism	2

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
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	IC50	=	1040.0	ug.mL-1	PMID[9207950]
NPT81	Cell line	A549	Homo sapiens	ED50	=	2.5	10'-1 ug/ml	PMID[8904848]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	6.3	10'-1 ug/ml	PMID[8904848]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	4.1	10'-5 ug/ml	PMID[8904848]
NPT81	Cell line	A549	Homo sapiens	ED50	=	2.5	10'-1 ug/ml	PMID[8021648]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	6.3	10'-1 ug/ml	PMID[8021648]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	4.1	10'-5 ug/ml	PMID[8021648]
NPT2802	Organism	Blattella germanica	Blattella germanica	Ratio	=	0.9	n.a.	PMID[10096871]
NPT2802	Organism	Blattella germanica	Blattella germanica	Ratio	=	1.5	n.a.	PMID[10096871]
NPT27	Others	Unspecified	n.a.	Activity	=	0.97	n.a.	PMID[9207950]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference
-	Artemia	LC50	=	1.4	ug.mL-1	PMID[8021648]
-	Artemia	LC50	=	2.6	ug.mL-1	PMID[8904848]

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 NPC488252 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	17443
0.1-0.2	29873
0.2-0.3	2230
0.3-0.4	85
0.4-0.5	25
0.5-0.6	70
0.6-0.7	66
0.7-0.8	0
0.8-0.85	3
0.85-0.9	7
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC231096
1.0	High Similarity	NPC475581
1.0	High Similarity	NPC62118
1.0	High Similarity	NPC107717
0.9388	High Similarity	NPC473478
0.9388	High Similarity	NPC473651
0.9388	High Similarity	NPC66346
0.92	High Similarity	NPC283085
0.92	High Similarity	NPC132496
0.92	High Similarity	NPC606740
0.92	High Similarity	NPC608614
0.88	High Similarity	NPC20621
0.88	High Similarity	NPC318963
0.88	High Similarity	NPC605101
0.8679	High Similarity	NPC480081
0.8654	High Similarity	NPC233551
0.8654	High Similarity	NPC40376
0.8654	High Similarity	NPC21208
0.8333	Intermediate Similarity	NPC91067
0.8077	Intermediate Similarity	NPC329615
0.807	Intermediate Similarity	NPC279267
0.7843	Intermediate Similarity	NPC134865
0.7843	Intermediate Similarity	NPC103523
0.7843	Intermediate Similarity	NPC488627
0.7843	Intermediate Similarity	NPC488631
0.7778	Intermediate Similarity	NPC169511
0.7778	Intermediate Similarity	NPC287164
0.7778	Intermediate Similarity	NPC234077
0.7547	Intermediate Similarity	NPC65930
0.74	Intermediate Similarity	NPC606043
0.7308	Intermediate Similarity	NPC232555
0.7308	Intermediate Similarity	NPC171174
0.7308	Intermediate Similarity	NPC114694
0.7308	Intermediate Similarity	NPC485248
0.7308	Intermediate Similarity	NPC142117
0.7308	Intermediate Similarity	NPC480249
0.7308	Intermediate Similarity	NPC485249
0.7308	Intermediate Similarity	NPC240695
0.7255	Intermediate Similarity	NPC107986
0.7255	Intermediate Similarity	NPC223871
0.7255	Intermediate Similarity	NPC231009
0.7255	Intermediate Similarity	NPC103284
0.7255	Intermediate Similarity	NPC110710
0.7255	Intermediate Similarity	NPC1083
0.7255	Intermediate Similarity	NPC82795
0.7255	Intermediate Similarity	NPC286338
0.7255	Intermediate Similarity	NPC603931
0.7255	Intermediate Similarity	NPC604237
0.717	Intermediate Similarity	NPC488632
0.717	Intermediate Similarity	NPC47937
0.717	Intermediate Similarity	NPC477011
0.7167	Intermediate Similarity	NPC482766
0.7143	Intermediate Similarity	NPC258068
0.7143	Intermediate Similarity	NPC476583
0.7115	Intermediate Similarity	NPC488253
0.7115	Intermediate Similarity	NPC473669
0.7115	Intermediate Similarity	NPC488251
0.7037	Intermediate Similarity	NPC280621
0.7037	Intermediate Similarity	NPC48338
0.7037	Intermediate Similarity	NPC241360
0.7037	Intermediate Similarity	NPC293136
0.7037	Intermediate Similarity	NPC488628
0.7018	Intermediate Similarity	NPC480082
0.6981	Remote Similarity	NPC81045
0.6981	Remote Similarity	NPC39754
0.6981	Remote Similarity	NPC171135
0.6981	Remote Similarity	NPC182383
0.6981	Remote Similarity	NPC61257
0.6981	Remote Similarity	NPC320569
0.6981	Remote Similarity	NPC133730
0.6981	Remote Similarity	NPC191929
0.6981	Remote Similarity	NPC100454
0.6981	Remote Similarity	NPC242364
0.6981	Remote Similarity	NPC172821
0.6981	Remote Similarity	NPC274446
0.6981	Remote Similarity	NPC485251
0.6981	Remote Similarity	NPC151403
0.6981	Remote Similarity	NPC261952
0.6981	Remote Similarity	NPC605171
0.6909	Remote Similarity	NPC42598
0.6852	Remote Similarity	NPC93794
0.6852	Remote Similarity	NPC473504
0.6852	Remote Similarity	NPC81778
0.6852	Remote Similarity	NPC40066
0.6833	Remote Similarity	NPC473663
0.6833	Remote Similarity	NPC473723
0.6833	Remote Similarity	NPC475173
0.6786	Remote Similarity	NPC329838
0.6786	Remote Similarity	NPC602738
0.678	Remote Similarity	NPC488630
0.678	Remote Similarity	NPC488625
0.678	Remote Similarity	NPC322529
0.678	Remote Similarity	NPC488626
0.6724	Remote Similarity	NPC320458
0.6667	Remote Similarity	NPC253801
0.6607	Remote Similarity	NPC178215
0.6607	Remote Similarity	NPC473687
0.6607	Remote Similarity	NPC204686
0.6607	Remote Similarity	NPC219498
0.6607	Remote Similarity	NPC308412
0.6607	Remote Similarity	NPC134885
0.6607	Remote Similarity	NPC488247
0.6607	Remote Similarity	NPC210218
0.6607	Remote Similarity	NPC488248
0.6531	Remote Similarity	NPC608138
0.6491	Remote Similarity	NPC488250
0.6441	Remote Similarity	NPC488623
0.6441	Remote Similarity	NPC488624
0.6441	Remote Similarity	NPC488629
0.6429	Remote Similarity	NPC480079
0.6379	Remote Similarity	NPC69082
0.6379	Remote Similarity	NPC488249
0.6316	Remote Similarity	NPC473904
0.6296	Remote Similarity	NPC329829
0.6271	Remote Similarity	NPC130359
0.6271	Remote Similarity	NPC14901
0.625	Remote Similarity	NPC488246
0.625	Remote Similarity	NPC480080
0.6226	Remote Similarity	NPC112685
0.6207	Remote Similarity	NPC134807
0.6102	Remote Similarity	NPC20339
0.6071	Remote Similarity	NPC156804
0.6066	Remote Similarity	NPC239517
0.6	Remote Similarity	NPC100921
0.6	Remote Similarity	NPC475159
0.6	Remote Similarity	NPC131002
0.6	Remote Similarity	NPC473780
0.6	Remote Similarity	NPC477018
0.6	Remote Similarity	NPC604521
0.5965	Remote Similarity	NPC600524
0.5965	Remote Similarity	NPC608355
0.5902	Remote Similarity	NPC477014
0.5902	Remote Similarity	NPC477013
0.5862	Remote Similarity	NPC219652
0.5862	Remote Similarity	NPC473840
0.5833	Remote Similarity	NPC473707
0.5763	Remote Similarity	NPC132940
0.5741	Remote Similarity	NPC73310
0.5741	Remote Similarity	NPC473529
0.5741	Remote Similarity	NPC180363
0.5741	Remote Similarity	NPC94875
0.5741	Remote Similarity	NPC11332
0.5741	Remote Similarity	NPC145914
0.5741	Remote Similarity	NPC601174
0.5741	Remote Similarity	NPC601403
0.5741	Remote Similarity	NPC603568
0.5741	Remote Similarity	NPC604330
0.5741	Remote Similarity	NPC608300
0.5741	Remote Similarity	NPC611200
0.5741	Remote Similarity	NPC611571
0.5738	Remote Similarity	NPC473995
0.5738	Remote Similarity	NPC488244
0.5714	Remote Similarity	NPC473520
0.569	Remote Similarity	NPC473649
0.569	Remote Similarity	NPC473156
0.569	Remote Similarity	NPC154097
0.569	Remote Similarity	NPC163093
0.569	Remote Similarity	NPC159750
0.569	Remote Similarity	NPC73248
0.569	Remote Similarity	NPC282815
0.569	Remote Similarity	NPC470401
0.569	Remote Similarity	NPC600956
0.569	Remote Similarity	NPC610454
0.5667	Remote Similarity	NPC20533
0.5593	Remote Similarity	NPC473671
0.5593	Remote Similarity	NPC475268
0.5593	Remote Similarity	NPC470400
0.5593	Remote Similarity	NPC25703
0.5593	Remote Similarity	NPC77871
0.5593	Remote Similarity	NPC9678
0.5593	Remote Similarity	NPC319036
0.5593	Remote Similarity	NPC604764
0.5593	Remote Similarity	NPC605867
0.5577	Remote Similarity	NPC609415
0.5574	Remote Similarity	NPC477012
0.5439	Remote Similarity	NPC25764
0.5439	Remote Similarity	NPC235809
0.5439	Remote Similarity	NPC39279
0.5439	Remote Similarity	NPC39167
0.5439	Remote Similarity	NPC292809
0.5439	Remote Similarity	NPC202055
0.5439	Remote Similarity	NPC606804
0.5439	Remote Similarity	NPC607425
0.5439	Remote Similarity	NPC608574
0.541	Remote Similarity	NPC309211
0.541	Remote Similarity	NPC485250
0.541	Remote Similarity	NPC477010
0.5373	Remote Similarity	NPC477017
0.5373	Remote Similarity	NPC477016
0.5333	Remote Similarity	NPC475616
0.5238	Remote Similarity	NPC120398
0.5238	Remote Similarity	NPC471567
0.5167	Remote Similarity	NPC144415
0.5167	Remote Similarity	NPC607439
0.5167	Remote Similarity	NPC608157
0.5156	Remote Similarity	NPC89001
0.5152	Remote Similarity	NPC473905
0.5152	Remote Similarity	NPC477015
0.5079	Remote Similarity	NPC139418

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6557
0.1-0.2	2548
0.2-0.3	45
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