NPASS Compound

Natural Product: NPC488244

Natural Product ID	NPC488244
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CPMBETMZGIWCGO-GSCSMLAHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10438659
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 109109 0 0 0 0 0 0 0 0999 V2000 -14.9463 3.8629 -1.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7887 3.0534 -1.3044 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.2897 1.7732 -0.6821 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1536 0.9467 -0.1270 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1731 0.5727 -1.1925 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0491 -0.2769 -0.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0516 -0.6497 -1.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9355 -1.5005 -1.1484 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9029 -1.1555 -0.1676 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3356 -0.9248 1.2366 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1267 -0.6692 2.1557 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1616 -1.7946 2.2171 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0182 -1.5715 3.1181 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7609 -1.5518 2.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2967 -1.7400 1.3351 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4063 -2.9159 1.1331 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1994 -2.8500 2.0096 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4105 -1.5967 1.6990 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8714 -1.5654 2.5156 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6424 -0.3429 2.2257 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1360 -0.1401 0.8404 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0828 -1.2467 0.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6160 -1.0502 -0.9781 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3982 0.1880 -1.2205 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6166 0.2487 -0.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8428 -0.7000 0.3955 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4973 1.4413 -0.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6475 1.2031 -1.3057 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4911 0.0755 -0.8247 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0763 0.2214 0.5079 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9709 1.3098 0.8764 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2747 1.5033 0.2284 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3671 1.7483 -1.2229 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8538 1.9118 -1.5179 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6122 1.1939 -2.3103 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9797 1.6946 -2.3008 C 0 0 2 0 0 0 0 0 0 0 0 0 15.8574 0.5922 -1.7038 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9869 2.7844 -1.4229 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7050 2.9370 -0.9371 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3734 3.8424 -0.1176 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1493 0.4281 0.5227 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1036 -1.6630 0.3471 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3170 -3.9258 1.7233 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.8802 3.9560 -2.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8783 3.3138 -1.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9699 4.8602 -1.3673 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2551 3.6718 -0.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0875 2.7584 -2.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0255 2.0321 0.1050 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8319 1.1695 -1.4634 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5746 0.0438 0.3857 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6793 1.5376 0.6825 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5977 -0.1272 -1.9302 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6588 1.4431 -1.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6595 0.4167 0.2379 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5825 -1.1495 -0.1013 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5544 -1.1495 -2.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6122 0.3018 -1.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3152 -2.5444 -0.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3502 -1.8031 -2.0993 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3118 -0.2418 -0.5535 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0705 -1.9398 -0.1825 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9792 -1.7055 1.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8382 0.0981 1.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5997 -0.5071 3.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6753 0.2648 1.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7568 -2.6325 2.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8855 -2.2743 1.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2092 -1.4124 4.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0175 -1.3756 3.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7193 -0.8349 1.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1390 -1.7112 0.5918 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9433 -3.8928 1.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0359 -2.9373 0.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4366 -2.8855 3.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0437 -0.7319 1.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4518 -2.4810 2.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5832 -1.5983 3.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5175 -0.2199 2.9084 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9616 0.5377 2.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4010 0.0727 0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7963 0.7806 0.8763 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8560 -1.3933 1.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5325 -2.2393 0.3663 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 -1.9621 -1.2453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7488 -1.0388 -1.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7560 1.0850 -1.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6616 0.2209 -2.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8755 1.6516 0.6303 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9038 2.3101 -0.7632 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2049 0.8692 -2.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2164 2.1161 -1.5685 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7624 -0.8077 -0.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1477 -0.2791 -1.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2338 0.2038 1.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6106 -0.7488 0.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2280 1.1306 1.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4274 2.3146 0.9870 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7748 2.3870 0.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0882 0.8648 -1.7917 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9095 2.6888 -1.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2483 0.3272 -2.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 15.3515 1.9675 -3.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7740 1.0645 -1.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0592 -0.1059 -2.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2395 0.0685 -0.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7487 -0.1121 1.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1182 -2.6105 0.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8259 -4.7768 1.6098 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 2 0 32 41 1 0 18 42 1 0 17 43 1 0 39 34 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 1 18 76 1 6 19 77 1 0 19 78 1 0 20 79 1 0 20 80 1 0 21 81 1 0 21 82 1 0 22 83 1 0 22 84 1 0 23 85 1 0 23 86 1 0 24 87 1 0 24 88 1 0 27 89 1 0 27 90 1 0 28 91 1 0 28 92 1 0 29 93 1 0 29 94 1 0 30 95 1 0 30 96 1 0 31 97 1 0 31 98 1 0 32 99 1 1 33100 1 0 33101 1 0 35102 1 0 36103 1 6 37104 1 0 37105 1 0 37106 1 0 41107 1 0 42108 1 0 43109 1 0 M END

Standard InCHIKey	CPMBETMZGIWCGO-GSCSMLAHSA-N
Standard InCHI	InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-22-27-35(40)36(41)28-23-17-16-19-24-33(38)25-20-18-21-26-34(39)30-32-29-31(2)43-37(32)42/h14-15,29,31,34-36,39-41H,3-13,16-28,30H2,1-2H3/b15-14-/t31-,34+,35+,36+/m0/s1
SMILES	CCCCCCCCCCCC/C=CCC[C@H]([C@@H](CCCCCCC(=O)CCCCC[C@H](CC1=C[C@H](C)OC1=O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	606.49	Volume:	682.147 ? Van der Waals volume.
Dense:	0.889	LogP:	6.415 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.203 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.499 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	30.0	Rigid Bonds:	8.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	1.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.043	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.22	Fsp³:	0.838
MCE-18:	20.294 ? 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:	0.724	Fluc inhibitor:	0.142 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.139 ? 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:	0.654	Promiscuous compounds:	0.409

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.088	MDCK Permeability:	-4.774
Pgp-inhibitor:	0.004	Pgp-substrate:	0.05
PAMPA:	0.002 ? 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%):	0.692	30% Bioavailability (F30%):	0.977
50% Bioavailability (F50%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.936
Plasma Protein Binding (PPB):	97.983%	Volume Distribution (VD):	0.114
Fu:	0.992% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.564
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.816
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.267
CYP2C9-inhibitor:	0.319	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.996
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.159 ? 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):

5.421

Half-life (T1/2):

1.162

ADMET: Toxicity

hERG Blockers:	0.473	hERG Blockers (10um):	0.817
Human Hepatotoxicity (H-HT):	0.506	Drug-induced Liver Injury (DILI):	0.029
AMES Toxicity:	0.3	Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.919	Skin Sensitization:	1.0
Carcinogencity:	0.242	Eye Corrosion:	0.091
Eye Irritation:	0.751	Respiratory Toxicity:	0.852
Drug-induced Neurotoxicity:	0.036	Ototoxicity:	0.524
Hematotoxicity:	0.033	Drug-induced Nephrotoxicity:	0.955
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.122
A549 Cytotoxicity:	0.98	Hek293 Cytotoxicity:	0.5
BCF:	0.738 ? 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:	4.691 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.267 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.883 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[7623031]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[7714532]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[8021648]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1201	Xylopia aromatica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	3

Activity Type	# Activity
Cell line	3

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.08	10'-2 ug/ml	PMID[7623031]
NPT83	Cell line	MCF7	Homo sapiens	ED50	<	1.0	10'-2 ug/ml	PMID[7623031]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.58	ug ml-1	PMID[7623031]

In vivo activity

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

Experimental ADME

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

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference
-	Artemia	LC50	=	9.33	ug.mL-1	PMID[7623031]

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 NPC488244 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	17417
0.1-0.2	29103
0.2-0.3	2908
0.3-0.4	220
0.4-0.5	94
0.5-0.6	88
0.6-0.7	20
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC488246
0.8077	Intermediate Similarity	NPC600188
0.7843	Intermediate Similarity	NPC480080
0.7288	Intermediate Similarity	NPC488245
0.6909	Remote Similarity	NPC473687
0.6909	Remote Similarity	NPC204686
0.6909	Remote Similarity	NPC219498
0.6909	Remote Similarity	NPC308412
0.6909	Remote Similarity	NPC134885
0.6909	Remote Similarity	NPC488247
0.6909	Remote Similarity	NPC210218
0.6909	Remote Similarity	NPC488248
0.6786	Remote Similarity	NPC488250
0.678	Remote Similarity	NPC480081
0.6667	Remote Similarity	NPC69082
0.6667	Remote Similarity	NPC488249
0.6531	Remote Similarity	NPC608138
0.6491	Remote Similarity	NPC134807
0.625	Remote Similarity	NPC134865
0.625	Remote Similarity	NPC103523
0.625	Remote Similarity	NPC488627
0.625	Remote Similarity	NPC488631
0.614	Remote Similarity	NPC480079
0.6094	Remote Similarity	NPC279267
0.5833	Remote Similarity	NPC473478
0.5833	Remote Similarity	NPC473651
0.5833	Remote Similarity	NPC66346
0.5833	Remote Similarity	NPC477012
0.5818	Remote Similarity	NPC606043
0.5738	Remote Similarity	NPC231096
0.5738	Remote Similarity	NPC475581
0.5738	Remote Similarity	NPC283085
0.5738	Remote Similarity	NPC62118
0.5738	Remote Similarity	NPC107717
0.5738	Remote Similarity	NPC130359
0.5738	Remote Similarity	NPC488252
0.5738	Remote Similarity	NPC14901
0.5714	Remote Similarity	NPC107986
0.5714	Remote Similarity	NPC223871
0.5714	Remote Similarity	NPC231009
0.5714	Remote Similarity	NPC103284
0.5714	Remote Similarity	NPC110710
0.5714	Remote Similarity	NPC1083
0.5714	Remote Similarity	NPC82795
0.5714	Remote Similarity	NPC286338
0.5714	Remote Similarity	NPC603931
0.5714	Remote Similarity	NPC604237
0.569	Remote Similarity	NPC477011
0.5667	Remote Similarity	NPC309211
0.5667	Remote Similarity	NPC477010
0.5645	Remote Similarity	NPC233551
0.5645	Remote Similarity	NPC40376
0.5645	Remote Similarity	NPC21208
0.5636	Remote Similarity	NPC112685
0.5625	Remote Similarity	NPC253801
0.5614	Remote Similarity	NPC488253
0.5614	Remote Similarity	NPC473669
0.5614	Remote Similarity	NPC488251
0.5606	Remote Similarity	NPC482766
0.5577	Remote Similarity	NPC609415
0.5517	Remote Similarity	NPC81045
0.5517	Remote Similarity	NPC232555
0.5517	Remote Similarity	NPC39754
0.5517	Remote Similarity	NPC171135
0.5517	Remote Similarity	NPC171174
0.5517	Remote Similarity	NPC182383
0.5517	Remote Similarity	NPC114694
0.5517	Remote Similarity	NPC61257
0.5517	Remote Similarity	NPC320569
0.5517	Remote Similarity	NPC485248
0.5517	Remote Similarity	NPC133730
0.5517	Remote Similarity	NPC191929
0.5517	Remote Similarity	NPC142117
0.5517	Remote Similarity	NPC100454
0.5517	Remote Similarity	NPC242364
0.5517	Remote Similarity	NPC480249
0.5517	Remote Similarity	NPC172821
0.5517	Remote Similarity	NPC485249
0.5517	Remote Similarity	NPC274446
0.5517	Remote Similarity	NPC485251
0.5517	Remote Similarity	NPC151403
0.5517	Remote Similarity	NPC240695
0.5517	Remote Similarity	NPC261952
0.5517	Remote Similarity	NPC605171
0.5484	Remote Similarity	NPC132496
0.5484	Remote Similarity	NPC606740
0.5484	Remote Similarity	NPC608614
0.5469	Remote Similarity	NPC91067
0.5424	Remote Similarity	NPC93794
0.5424	Remote Similarity	NPC488632
0.5424	Remote Similarity	NPC473504
0.5424	Remote Similarity	NPC144415
0.5424	Remote Similarity	NPC81778
0.5424	Remote Similarity	NPC40066
0.5424	Remote Similarity	NPC47937
0.5424	Remote Similarity	NPC607439
0.5424	Remote Similarity	NPC608157
0.5397	Remote Similarity	NPC480082
0.5333	Remote Similarity	NPC280621
0.5333	Remote Similarity	NPC48338
0.5333	Remote Similarity	NPC488628
0.5246	Remote Similarity	NPC178215
0.5246	Remote Similarity	NPC42598
0.5231	Remote Similarity	NPC322529
0.5161	Remote Similarity	NPC20621
0.5161	Remote Similarity	NPC318963
0.5161	Remote Similarity	NPC602738
0.5161	Remote Similarity	NPC605101
0.5161	Remote Similarity	NPC605396
0.5079	Remote Similarity	NPC473707
0.5079	Remote Similarity	NPC11456
0.5079	Remote Similarity	NPC20339

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6364
0.1-0.2	2697
0.2-0.3	86
0.3-0.4	2
0.4-0.5	1
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