NPASS Compound

Natural Product: NPC488249

Natural Product ID	NPC488249
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MYIILGWLOBYDNH-WLAZQFJTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10438900
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 110111 0 0 0 0 0 0 0 0999 V2000 -14.1785 -2.2257 -2.2188 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7364 -0.7978 -2.1529 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2027 -0.7199 -1.9340 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9145 -1.4220 -0.6496 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5350 -1.5355 -0.1727 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7200 -0.3946 0.2266 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4294 0.6754 -0.7485 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5075 1.7197 -0.1047 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2033 1.1876 0.3411 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3988 0.6278 -0.8280 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1317 1.6789 -1.8025 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9137 2.0623 -2.1133 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7234 1.4716 -1.5138 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9025 2.5076 -0.7295 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7247 1.7762 -0.1552 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8109 2.6328 0.6715 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5319 2.9668 1.9750 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5720 1.6114 2.6387 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 0.9017 2.0001 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5604 0.5496 3.1069 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9303 0.1612 2.5036 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8807 -0.1962 3.5928 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2583 -0.4596 3.1833 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6532 -1.5130 2.2388 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2300 -1.4259 0.8325 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7671 -2.5754 -0.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2861 -2.6253 -0.0257 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8919 -1.3709 -0.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3984 -1.4531 -0.5047 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9906 -2.5601 -1.2891 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4531 -2.7231 -1.2752 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3387 -1.6552 -1.7732 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2906 -0.3448 -1.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0126 0.8190 -1.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0513 1.9181 -0.7220 C 0 0 2 0 0 0 0 0 0 0 0 0 12.2019 2.8891 -1.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3894 1.3054 0.4871 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5323 -0.0316 0.2965 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8291 -0.9173 1.1660 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8352 -3.9109 -1.9652 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8459 -3.1485 1.0922 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 1.7393 3.8194 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2189 1.8314 1.1690 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0144 1.2146 -1.2373 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2850 -2.8283 -2.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0219 -2.3297 -2.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4337 -2.5535 -1.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1838 -0.3144 -1.2713 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0075 -0.1960 -3.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8023 -1.2854 -2.8228 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9387 0.3232 -2.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5849 -1.0215 0.1814 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3194 -2.4815 -0.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5593 -2.2393 0.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8971 -2.1717 -0.8805 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7435 -0.8363 0.6493 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1238 0.1218 1.1574 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3826 1.2689 -0.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0444 0.3993 -1.7176 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0648 2.2234 0.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3565 2.5072 -0.8645 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6470 2.0470 0.8128 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2488 0.4251 1.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1319 -0.1057 -1.3089 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5777 0.0027 -0.5036 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0014 2.1654 -2.3011 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8017 2.8703 -2.8678 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8108 0.5394 -0.9827 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0326 1.2285 -2.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5359 3.3042 -1.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5389 2.9955 0.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1266 0.9340 0.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4181 3.5000 0.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5419 3.3828 1.7850 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 3.6269 2.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4912 1.0342 2.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4604 1.6881 3.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6702 -0.0234 1.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2080 -0.1902 3.8168 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6590 -0.8190 1.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3056 0.9277 1.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8996 0.6086 4.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4930 -1.1391 4.1376 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9146 -0.5309 4.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6603 0.5444 2.7478 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3865 -2.5444 2.6733 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8026 -1.5712 2.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5259 -0.4879 0.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1455 -1.5076 0.7217 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3898 -3.5413 0.3067 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4475 -2.3608 -1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4951 -3.4031 -0.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5161 -1.0747 -1.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6203 -0.5506 0.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7243 -1.3800 0.5381 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7176 -0.4546 -0.9551 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4864 -3.5175 -0.9489 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6876 -2.4069 -2.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7325 -2.8841 -0.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3980 -2.0730 -1.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1113 -1.5037 -2.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7884 0.9121 -2.7570 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0891 2.4788 -0.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4647 3.3553 -0.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0644 2.2446 -1.3163 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9300 3.6085 -1.8030 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1529 -3.6289 -2.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6651 -2.7891 1.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3306 2.3806 3.2198 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2496 0.2494 -1.3434 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 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 31 40 1 0 27 41 1 0 20 42 1 0 19 43 1 0 15 44 1 0 43 16 1 0 38 33 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 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 6 20 79 1 1 21 80 1 0 21 81 1 0 22 82 1 0 22 83 1 0 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 25 88 1 0 25 89 1 0 26 90 1 0 26 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 1 32100 1 0 32101 1 0 34102 1 0 35103 1 1 36104 1 0 36105 1 0 36106 1 0 40107 1 0 41108 1 0 42109 1 0 44110 1 0 M END

Standard InCHIKey	MYIILGWLOBYDNH-WLAZQFJTSA-N
Standard InCHI	InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-13-17-23-33(40)35-25-26-36(44-35)34(41)24-18-15-14-16-20-31(38)21-19-22-32(39)28-30-27-29(2)43-37(30)42/h12-13,27,29,31-36,38-41H,3-11,14-26,28H2,1-2H3/b13-12-/t29-,31?,32+,33+,34+,35+,36+/m0/s1
SMILES	CCCCCCCCCC/C=CCC[C@H]([C@H]1CC[C@H]([C@@H](CCCCCCC(CCC[C@H](CC2=C[C@H](C)OC2=O)O)O)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.48	Volume:	685.017 ? Van der Waals volume.
Dense:	0.909	LogP:	5.681 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.109 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.676 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	27.0	Rigid Bonds:	12.0
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:	0.042	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.772	Fsp³:	0.865
MCE-18:	32.174 ? 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:	0.772	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.084 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.58	Promiscuous compounds:	0.143

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.172	MDCK Permeability:	-4.796
Pgp-inhibitor:	0.018	Pgp-substrate:	0.446
PAMPA:	0.193 ? 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):	0.003
20% Bioavailability (F20%):	0.957	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.885
Plasma Protein Binding (PPB):	96.193%	Volume Distribution (VD):	-0.2
Fu:	3.432% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.23
OATP1B3 inhibitor:	0.927	BCRP inhibitor:	0.753
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.51	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.652	CYP2D6-substrate:	0.952
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.979
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
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):

6.782

Half-life (T1/2):

1.036

ADMET: Toxicity

hERG Blockers:	0.453	hERG Blockers (10um):	0.776
Human Hepatotoxicity (H-HT):	0.574	Drug-induced Liver Injury (DILI):	0.022
AMES Toxicity:	0.259	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.922	Skin Sensitization:	1.0
Carcinogencity:	0.205	Eye Corrosion:	0.014
Eye Irritation:	0.563	Respiratory Toxicity:	0.847
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.891
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.965
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.1
A549 Cytotoxicity:	0.955	Hek293 Cytotoxicity:	0.345
BCF:	1.246 ? 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:	5.135 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.319 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.275 ? 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	=	3.64	10'-3 ug/ml	PMID[7714532]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	7.11	10'-3 ug/ml	PMID[7714532]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	7.26	10'-3 ug/ml	PMID[7714532]

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	=	0.871	ug.mL-1	PMID[7714532]

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 NPC488249 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	17264
0.1-0.2	29445
0.2-0.3	2728
0.3-0.4	184
0.4-0.5	28
0.5-0.6	40
0.6-0.7	80
0.7-0.8	0
0.8-0.85	17
0.85-0.9	12
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC69082
0.9787	High Similarity	NPC488250
0.8723	High Similarity	NPC488253
0.8723	High Similarity	NPC488251
0.8511	High Similarity	NPC107986
0.8511	High Similarity	NPC223871
0.8511	High Similarity	NPC231009
0.8511	High Similarity	NPC103284
0.8511	High Similarity	NPC110710
0.8511	High Similarity	NPC1083
0.8511	High Similarity	NPC82795
0.8511	High Similarity	NPC286338
0.8511	High Similarity	NPC603931
0.8511	High Similarity	NPC604237
0.8367	Intermediate Similarity	NPC488632
0.8333	Intermediate Similarity	NPC473669
0.8298	Intermediate Similarity	NPC606043
0.8235	Intermediate Similarity	NPC309211
0.8163	Intermediate Similarity	NPC232555
0.8163	Intermediate Similarity	NPC171174
0.8163	Intermediate Similarity	NPC114694
0.8163	Intermediate Similarity	NPC485248
0.8163	Intermediate Similarity	NPC142117
0.8163	Intermediate Similarity	NPC480249
0.8163	Intermediate Similarity	NPC485249
0.8163	Intermediate Similarity	NPC240695
0.8039	Intermediate Similarity	NPC178215
0.8	Intermediate Similarity	NPC134865
0.8	Intermediate Similarity	NPC103523
0.8	Intermediate Similarity	NPC488627
0.8	Intermediate Similarity	NPC488631
0.78	Intermediate Similarity	NPC182383
0.7647	Intermediate Similarity	NPC93794
0.7647	Intermediate Similarity	NPC473504
0.7647	Intermediate Similarity	NPC488246
0.7647	Intermediate Similarity	NPC81778
0.7647	Intermediate Similarity	NPC40066
0.7647	Intermediate Similarity	NPC477011
0.7647	Intermediate Similarity	NPC607439
0.75	Intermediate Similarity	NPC280621
0.75	Intermediate Similarity	NPC48338
0.75	Intermediate Similarity	NPC488628
0.7451	Intermediate Similarity	NPC81045
0.7451	Intermediate Similarity	NPC39754
0.7451	Intermediate Similarity	NPC171135
0.7451	Intermediate Similarity	NPC61257
0.7451	Intermediate Similarity	NPC320569
0.7451	Intermediate Similarity	NPC133730
0.7451	Intermediate Similarity	NPC191929
0.7451	Intermediate Similarity	NPC100454
0.7451	Intermediate Similarity	NPC242364
0.7451	Intermediate Similarity	NPC172821
0.7451	Intermediate Similarity	NPC274446
0.7451	Intermediate Similarity	NPC485251
0.7451	Intermediate Similarity	NPC151403
0.7451	Intermediate Similarity	NPC261952
0.7451	Intermediate Similarity	NPC605171
0.7358	Intermediate Similarity	NPC42598
0.7358	Intermediate Similarity	NPC473687
0.7358	Intermediate Similarity	NPC204686
0.7358	Intermediate Similarity	NPC219498
0.7358	Intermediate Similarity	NPC308412
0.7358	Intermediate Similarity	NPC134885
0.7358	Intermediate Similarity	NPC488247
0.7358	Intermediate Similarity	NPC210218
0.7358	Intermediate Similarity	NPC488248
0.7308	Intermediate Similarity	NPC47937
0.7222	Intermediate Similarity	NPC20621
0.7222	Intermediate Similarity	NPC318963
0.7222	Intermediate Similarity	NPC605101
0.7193	Intermediate Similarity	NPC480081
0.7059	Intermediate Similarity	NPC100921
0.7059	Intermediate Similarity	NPC475159
0.7059	Intermediate Similarity	NPC131002
0.7059	Intermediate Similarity	NPC473780
0.7059	Intermediate Similarity	NPC477018
0.7059	Intermediate Similarity	NPC604521
0.7021	Intermediate Similarity	NPC608138
0.6981	Remote Similarity	NPC480080
0.6964	Remote Similarity	NPC130359
0.6964	Remote Similarity	NPC14901
0.6909	Remote Similarity	NPC134807
0.6909	Remote Similarity	NPC602738
0.6842	Remote Similarity	NPC488623
0.6842	Remote Similarity	NPC488624
0.6842	Remote Similarity	NPC488629
0.6792	Remote Similarity	NPC156804
0.6786	Remote Similarity	NPC473478
0.6786	Remote Similarity	NPC473651
0.6786	Remote Similarity	NPC66346
0.6721	Remote Similarity	NPC279267
0.6667	Remote Similarity	NPC283085
0.6667	Remote Similarity	NPC112685
0.6667	Remote Similarity	NPC169511
0.6667	Remote Similarity	NPC287164
0.6667	Remote Similarity	NPC234077
0.6667	Remote Similarity	NPC488244
0.661	Remote Similarity	NPC488630
0.661	Remote Similarity	NPC488625
0.661	Remote Similarity	NPC488626
0.6607	Remote Similarity	NPC329838
0.6545	Remote Similarity	NPC473671
0.6545	Remote Similarity	NPC475268
0.6545	Remote Similarity	NPC470400
0.6545	Remote Similarity	NPC77871
0.6545	Remote Similarity	NPC9678
0.6545	Remote Similarity	NPC319036
0.6545	Remote Similarity	NPC604764
0.6545	Remote Similarity	NPC605867
0.6491	Remote Similarity	NPC20339
0.6471	Remote Similarity	NPC73310
0.6471	Remote Similarity	NPC473529
0.6471	Remote Similarity	NPC180363
0.6471	Remote Similarity	NPC94875
0.6471	Remote Similarity	NPC11332
0.6471	Remote Similarity	NPC145914
0.6471	Remote Similarity	NPC601174
0.6471	Remote Similarity	NPC601403
0.6471	Remote Similarity	NPC603568
0.6471	Remote Similarity	NPC604330
0.6471	Remote Similarity	NPC608300
0.6471	Remote Similarity	NPC611200
0.6471	Remote Similarity	NPC611571
0.6441	Remote Similarity	NPC239517
0.6379	Remote Similarity	NPC231096
0.6379	Remote Similarity	NPC475581
0.6379	Remote Similarity	NPC62118
0.6379	Remote Similarity	NPC258068
0.6379	Remote Similarity	NPC132496
0.6379	Remote Similarity	NPC107717
0.6379	Remote Similarity	NPC488252
0.6379	Remote Similarity	NPC476583
0.6364	Remote Similarity	NPC473649
0.6364	Remote Similarity	NPC473156
0.6364	Remote Similarity	NPC154097
0.6364	Remote Similarity	NPC163093
0.6364	Remote Similarity	NPC159750
0.6364	Remote Similarity	NPC73248
0.6364	Remote Similarity	NPC282815
0.6364	Remote Similarity	NPC470401
0.6364	Remote Similarity	NPC600956
0.6364	Remote Similarity	NPC610454
0.6333	Remote Similarity	NPC91067
0.6316	Remote Similarity	NPC20533
0.6316	Remote Similarity	NPC477010
0.6271	Remote Similarity	NPC233551
0.6271	Remote Similarity	NPC40376
0.6271	Remote Similarity	NPC21208
0.623	Remote Similarity	NPC253801
0.614	Remote Similarity	NPC132940
0.6129	Remote Similarity	NPC473663
0.6129	Remote Similarity	NPC473723
0.6129	Remote Similarity	NPC475173
0.6111	Remote Similarity	NPC329829
0.6102	Remote Similarity	NPC606740
0.6102	Remote Similarity	NPC608614
0.6	Remote Similarity	NPC477014
0.6	Remote Similarity	NPC477013
0.5965	Remote Similarity	NPC480079
0.5818	Remote Similarity	NPC25764
0.5818	Remote Similarity	NPC235809
0.5818	Remote Similarity	NPC39279
0.5818	Remote Similarity	NPC39167
0.5818	Remote Similarity	NPC292809
0.5818	Remote Similarity	NPC202055
0.5818	Remote Similarity	NPC606804
0.5818	Remote Similarity	NPC607425
0.5818	Remote Similarity	NPC608574
0.5806	Remote Similarity	NPC322529
0.5789	Remote Similarity	NPC144415
0.5789	Remote Similarity	NPC608157
0.5781	Remote Similarity	NPC488245
0.5738	Remote Similarity	NPC89001
0.5738	Remote Similarity	NPC480082
0.5692	Remote Similarity	NPC482766
0.569	Remote Similarity	NPC219652
0.569	Remote Similarity	NPC473840
0.569	Remote Similarity	NPC241360
0.569	Remote Similarity	NPC293136
0.5667	Remote Similarity	NPC473707
0.5667	Remote Similarity	NPC477012
0.5593	Remote Similarity	NPC473904
0.5574	Remote Similarity	NPC120398
0.5574	Remote Similarity	NPC471567
0.5556	Remote Similarity	NPC280612
0.5517	Remote Similarity	NPC600524
0.5517	Remote Similarity	NPC608355
0.5455	Remote Similarity	NPC477017
0.5455	Remote Similarity	NPC477016
0.541	Remote Similarity	NPC11456
0.5333	Remote Similarity	NPC65930
0.5246	Remote Similarity	NPC485250
0.5246	Remote Similarity	NPC600188
0.5246	Remote Similarity	NPC605396
0.5231	Remote Similarity	NPC475206
0.5167	Remote Similarity	NPC25703
0.5161	Remote Similarity	NPC139418
0.5079	Remote Similarity	NPC473995

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6537
0.1-0.2	2535
0.2-0.3	76
0.3-0.4	2
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