NPASS Compound

Natural Product: NPC480250

Natural Product ID	NPC480250
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DZWITTGSSIGAEW-RQYIPPDOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11801683
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 -12.5690 -0.2681 3.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3477 0.4475 3.9350 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7861 1.3298 2.8487 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3694 0.5830 1.6208 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2964 -0.4335 1.8229 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0255 0.0786 2.3508 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2455 1.1254 1.7211 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7064 0.9388 0.3356 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7058 0.8272 -0.7319 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3114 0.7766 -2.1474 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4264 -0.2256 -2.7269 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0070 -0.1611 -2.2623 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1542 -1.2261 -2.9266 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7327 -1.2487 -2.5178 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9393 -0.0147 -2.7525 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5061 -0.1854 -2.3022 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3518 -0.2799 -0.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8021 -1.2673 -0.6660 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7680 -1.9921 -1.9272 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0984 -2.4147 -2.4592 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8622 -1.3862 -3.2137 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3030 -0.1656 -2.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3190 -0.4569 -1.3822 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5462 -1.0952 -2.0057 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6311 -1.4380 -1.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2260 -0.2505 -0.3099 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8211 0.7456 -1.2419 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3846 1.9243 -0.5717 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5390 1.8007 0.3438 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4215 0.9432 1.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4034 1.6280 2.5367 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1859 1.1998 3.9461 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3855 -0.2715 4.0104 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4636 -1.0298 3.7860 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7088 -0.8586 4.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1337 3.0283 2.2323 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1675 4.0172 3.0073 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8186 3.1095 0.8868 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6522 0.7776 -0.8552 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8491 -3.1105 -1.5013 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1178 -1.2548 -2.9140 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4067 1.1045 -2.0230 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9521 0.3041 2.4550 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3220 -1.3092 3.0404 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3927 -0.3095 4.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7581 1.0962 4.7463 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6480 -0.2981 4.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9213 1.9059 3.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5525 2.1137 2.6273 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2872 -0.0121 1.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2040 1.2498 0.7493 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7247 -1.0680 2.7200 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2964 -1.1861 1.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1335 0.3232 3.4734 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3353 -0.8447 2.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3006 1.2585 2.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7009 2.1616 1.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2239 -0.1247 0.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8744 1.6154 0.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4791 0.0463 -0.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3500 1.7864 -0.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3051 0.7324 -2.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9686 1.8375 -2.4881 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3709 -0.0615 -3.8571 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8306 -1.2801 -2.6463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9083 -0.1195 -1.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5850 0.8274 -2.6567 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2488 -1.1270 -4.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6026 -2.2116 -2.6704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2112 -2.0672 -3.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5889 -1.5741 -1.4590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8877 0.2415 -3.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0930 0.7214 -2.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0346 0.6839 -0.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2478 -0.6231 -0.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6926 -0.7677 -0.3253 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4804 -1.9243 0.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1842 -2.9608 -1.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9143 -3.2474 -3.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6967 -1.8662 -3.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1670 -1.0399 -4.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5192 0.4876 -2.1200 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8979 0.4998 -3.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9180 -1.1146 -0.6147 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2015 -2.0642 -2.4668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8797 -0.4876 -2.8654 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2462 -2.1231 -0.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4568 -1.8964 -1.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0223 -0.6985 0.3099 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5098 0.1979 0.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0728 1.0733 -2.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5916 0.2046 -1.8805 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5954 2.5313 -0.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7241 2.6695 -1.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4799 1.4782 -0.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4301 0.9582 1.9890 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8392 -0.0912 1.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4014 1.3506 2.1390 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2427 1.5496 4.3727 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9994 1.6859 4.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0752 -1.5266 3.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4561 -0.0543 4.5984 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6696 -1.5011 5.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1787 0.9443 0.0154 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4595 -3.0695 -0.6147 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5696 0.7626 -1.1147 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 33 35 1 0 31 36 1 0 36 37 2 0 36 38 1 0 23 39 1 0 20 40 1 0 19 41 1 0 15 42 1 0 41 16 1 0 38 29 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 6 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 6 30 96 1 0 30 97 1 0 31 98 1 0 32 99 1 0 32100 1 0 35101 1 0 35102 1 0 35103 1 0 39104 1 0 40105 1 0 42106 1 0 M END

Standard InCHIKey	DZWITTGSSIGAEW-RQYIPPDOSA-N
Standard InCHI	InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-12-13-17-20-31(38)33-23-24-34(42-33)32(39)22-21-29(37)18-15-14-16-19-30-26-28(25-27(2)36)35(40)41-30/h28-34,37-39H,3-26H2,1-2H3/t28?,29-,30-,31-,32-,33-,34-/m1/s1
SMILES	CCCCCCCCCCCCCC[C@H]([C@H]1CC[C@H]([C@@H](CC[C@@H](CCCCC[C@@H]2CC(CC(=O)C)C(=O)O2)O)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.47	Volume:	653.062 ? Van der Waals volume.
Dense:	0.913	LogP:	5.476 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.8 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.446 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	Rigid Bonds:	12.0
TPSA:	113.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.071	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.574	Fsp³:	0.943
MCE-18:	33.088 ? 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:	0.798	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.538	Promiscuous compounds:	0.416

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.194	MDCK Permeability:	-4.855
Pgp-inhibitor:	0.001	Pgp-substrate:	0.849
PAMPA:	0.038 ? 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):	0.016
20% Bioavailability (F20%):	0.911	30% Bioavailability (F30%):	0.983
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.953
Plasma Protein Binding (PPB):	96.753%	Volume Distribution (VD):	0.675
Fu:	3.458% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.05
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.369
BSEP inhibitor:	0.785

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.016	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.051	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.761
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.043
HLM stability:	0.002 ? 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):

5.571

Half-life (T1/2):

0.924

ADMET: Toxicity

hERG Blockers:	0.405	hERG Blockers (10um):	0.74
Human Hepatotoxicity (H-HT):	0.679	Drug-induced Liver Injury (DILI):	0.084
AMES Toxicity:	0.024	Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.637	Skin Sensitization:	1.0
Carcinogencity:	0.136	Eye Corrosion:	0.622
Eye Irritation:	0.921	Respiratory Toxicity:	0.972
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.616
Hematotoxicity:	0.266	Drug-induced Nephrotoxicity:	0.881
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.944	Hek293 Cytotoxicity:	0.112
BCF:	1.05 ? 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:	5.095 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.312 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.119 ? 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
NPO6886	Asimina longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7494147]
NPO6886	Asimina longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8627602]
NPO6886	Asimina longifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6886	Asimina longifolia	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

Activity Type	# Activity
ED50	6

Activity Type	# Activity
Cell line	6

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	=	2.06	10'-5 ug/ml	PMID[7494147]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	9.67	10'-1 ug/ml	PMID[7494147]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	4.05	10'-4 ug/ml	PMID[7494147]
NPT376	Cell line	A498	Homo sapiens	ED50	=	2.91	10'-1 ug/ml	PMID[7494147]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	1.37	10'-1 ug/ml	PMID[7494147]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	1.33	10'-3 ug/ml	PMID[7494147]

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	=	0.14	ug.mL-1	PMID[7494147]

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 NPC480250 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	16957
0.1-0.2	30296
0.2-0.3	2290
0.3-0.4	99
0.4-0.5	122
0.5-0.6	52
0.6-0.7	1
0.7-0.8	0
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC480251
0.9556	High Similarity	NPC482767
0.9556	High Similarity	NPC475260
0.9556	High Similarity	NPC488621
0.9556	High Similarity	NPC473775
0.9556	High Similarity	NPC488622
0.8889	High Similarity	NPC474100
0.8889	High Similarity	NPC475232
0.8542	High Similarity	NPC475616
0.84	Intermediate Similarity	NPC480076
0.84	Intermediate Similarity	NPC480077
0.8125	Intermediate Similarity	NPC488234
0.8	Intermediate Similarity	NPC473699
0.8	Intermediate Similarity	NPC51249
0.7959	Intermediate Similarity	NPC480078
0.7959	Intermediate Similarity	NPC480071
0.7843	Intermediate Similarity	NPC480075
0.7018	Intermediate Similarity	NPC475206
0.6842	Remote Similarity	NPC473791
0.5849	Remote Similarity	NPC480072
0.5818	Remote Similarity	NPC232555
0.5818	Remote Similarity	NPC171174
0.5818	Remote Similarity	NPC114694
0.5818	Remote Similarity	NPC485248
0.5818	Remote Similarity	NPC142117
0.5818	Remote Similarity	NPC480249
0.5818	Remote Similarity	NPC485249
0.5818	Remote Similarity	NPC240695
0.5714	Remote Similarity	NPC488632
0.569	Remote Similarity	NPC20621
0.569	Remote Similarity	NPC318963
0.569	Remote Similarity	NPC605101
0.5636	Remote Similarity	NPC473669
0.5536	Remote Similarity	NPC156804
0.55	Remote Similarity	NPC258068
0.55	Remote Similarity	NPC476583
0.5472	Remote Similarity	NPC480074
0.5455	Remote Similarity	NPC107986
0.5455	Remote Similarity	NPC223871
0.5455	Remote Similarity	NPC231009
0.5455	Remote Similarity	NPC103284
0.5455	Remote Similarity	NPC110710
0.5455	Remote Similarity	NPC1083
0.5455	Remote Similarity	NPC82795
0.5455	Remote Similarity	NPC286338
0.5455	Remote Similarity	NPC603931
0.5455	Remote Similarity	NPC604237
0.5439	Remote Similarity	NPC47937
0.5357	Remote Similarity	NPC488253
0.5357	Remote Similarity	NPC488251
0.5345	Remote Similarity	NPC280621
0.5345	Remote Similarity	NPC48338
0.5345	Remote Similarity	NPC488628
0.5273	Remote Similarity	NPC606043
0.5263	Remote Similarity	NPC182383
0.5254	Remote Similarity	NPC42598
0.5179	Remote Similarity	NPC100921
0.5179	Remote Similarity	NPC475159
0.5179	Remote Similarity	NPC131002
0.5179	Remote Similarity	NPC473780
0.5179	Remote Similarity	NPC477018
0.5179	Remote Similarity	NPC604521
0.5172	Remote Similarity	NPC477011
0.5161	Remote Similarity	NPC477014
0.5161	Remote Similarity	NPC477013
0.5085	Remote Similarity	NPC241360
0.5085	Remote Similarity	NPC293136
0.5082	Remote Similarity	NPC473478
0.5082	Remote Similarity	NPC473651
0.5082	Remote Similarity	NPC139418
0.5082	Remote Similarity	NPC66346

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6130
0.1-0.2	2948
0.2-0.3	72
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