NPASS Compound

Natural Product: NPC473904

Natural Product ID	NPC473904
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Parisin
IUPAC Name	3-[(13S)-2,13-dihydroxy-13-[(2S,5S)-5-[(1S,4S,5R)-1,4,5-trihydroxypentadecyl]oxolan-2-yl]tridecyl]-5-hydroxy-5-methylfuran-2-one
Synonyms	Parisin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL454773
PubChem CID	44566775
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 114115 0 0 0 0 0 0 0 0999 V2000 -16.2046 0.3771 0.9145 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6334 -0.6920 0.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0882 -0.7375 0.1935 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5582 0.5933 -0.1716 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1419 0.9292 -0.0213 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0768 0.1828 -0.7236 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8402 -1.2320 -0.3630 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7174 -1.8902 -1.0625 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3600 -1.5133 -0.7237 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9272 -0.1212 -0.8348 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3939 -0.0169 -0.5659 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9357 1.3846 -0.6739 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6585 1.7117 -0.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3513 1.2011 -0.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8929 -0.1729 -0.2118 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3807 -0.2054 -0.6344 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8236 -1.5641 -0.5802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3558 -1.3947 0.3602 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2999 -0.0051 0.8316 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7127 0.6247 0.1643 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5853 0.7970 0.7095 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6279 0.3697 1.6838 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1575 -1.0069 1.6359 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.1687 2.7185 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3357 -0.2797 2.7437 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3253 -0.2496 1.6653 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9398 0.1144 0.2869 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1820 0.1293 -0.6326 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1947 1.1262 -0.2079 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3652 1.1061 -1.1828 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0474 -0.2389 -1.2288 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2028 -0.2563 -2.1671 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3301 0.6636 -1.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0916 0.5247 -0.6911 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3963 0.2059 -0.7236 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8908 0.1389 0.6522 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8093 0.4799 1.4767 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6809 0.7077 0.6677 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5419 1.0193 1.1558 O 0 0 0 0 0 0 0 0 0 0 0 0 16.0624 1.0914 0.8525 C 0 0 0 0 0 0 0 0 0 0 0 0 15.3152 -1.1926 0.8665 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7324 -0.1449 -3.5070 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1856 2.1024 1.1920 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8457 -0.6008 1.1361 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9088 2.1084 0.1456 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7219 -0.9126 -1.3550 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.6696 0.4008 1.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.2733 0.1157 1.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1967 1.3499 0.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8618 -0.4033 -1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.0343 -1.6943 0.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8009 -1.5028 -0.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8477 -1.1007 1.1789 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1587 1.3693 0.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8713 0.8567 -1.2487 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8804 0.9168 1.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0255 2.0633 -0.2226 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2134 0.8534 -0.8109 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3849 0.1311 -1.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6594 -1.2243 0.7746 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7561 -1.8595 -0.5420 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8177 -3.0280 -1.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8502 -1.7301 -2.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1244 -1.8446 0.3694 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6069 -2.2176 -1.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3816 0.5515 -0.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1060 0.3210 -1.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3125 -0.4130 0.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1412 1.8468 -1.6677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8406 1.6610 1.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5599 2.8761 -0.1351 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0121 1.5557 -1.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6058 1.8350 0.2606 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3031 -0.9847 -0.7777 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3284 0.1622 -1.6967 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -2.3203 -0.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4840 -1.9675 -1.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3143 -1.5942 -0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2453 -2.1464 1.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0203 -0.0134 1.9137 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9178 0.8977 -0.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1446 0.4952 2.7123 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5164 1.0709 1.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3561 -1.7706 1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4634 -1.3242 0.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6740 -1.2082 3.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5871 -2.2360 2.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9481 0.7665 2.9753 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8869 -0.5362 3.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1593 0.4570 2.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8988 -1.2302 1.5993 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4205 1.0918 0.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2959 -0.6504 -0.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8838 0.3104 -1.6731 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6119 -0.8996 -0.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7721 2.1457 -0.1313 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6100 0.8870 0.8120 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0983 1.8858 -0.9401 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8972 1.3465 -2.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1951 -0.7259 -0.2626 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2659 -0.9234 -1.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6025 -1.3273 -2.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9929 0.6175 -2.8436 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9953 1.7522 -1.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0248 0.0182 -1.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 16.4622 1.4486 -0.1317 H 0 0 0 0 0 0 0 0 0 0 0 0 16.8435 0.5892 1.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6800 2.0111 1.3542 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0811 -1.3657 1.8304 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3977 -1.0348 -3.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0349 1.9289 2.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0770 -1.5448 1.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6260 1.9569 1.1035 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6312 -1.8144 -0.9728 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 19 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 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 36 40 1 0 36 41 1 0 32 42 1 0 21 43 1 0 15 44 1 0 12 45 1 0 11 46 1 0 20 16 1 0 38 34 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 8 62 1 0 8 63 1 0 9 64 1 0 9 65 1 0 10 66 1 0 10 67 1 0 11 68 1 1 12 69 1 6 13 70 1 0 13 71 1 0 14 72 1 0 14 73 1 0 15 74 1 6 16 75 1 6 17 76 1 0 17 77 1 0 18 78 1 0 18 79 1 0 19 80 1 1 21 81 1 6 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 27 93 1 0 28 94 1 0 28 95 1 0 29 96 1 0 29 97 1 0 30 98 1 0 30 99 1 0 31100 1 0 31101 1 0 32102 1 0 33103 1 0 33104 1 0 35105 1 0 40106 1 0 40107 1 0 40108 1 0 41109 1 0 42110 1 0 43111 1 0 44112 1 0 45113 1 0 46114 1 0 M END

Standard InCHIKey	USIUGLRYYKXESD-ZAAOCBMESA-N
Standard InCHI	InChI=1S/C37H68O9/c1-3-4-5-6-7-11-14-17-20-30(39)31(40)22-23-33(42)35-25-24-34(45-35)32(41)21-18-15-12-9-8-10-13-16-19-29(38)26-28-27-37(2,44)46-36(28)43/h27,29-35,38-42,44H,3-26H2,1-2H3/t29?,30-,31+,32+,33+,34+,35+,37?/m1/s1
SMILES	CCCCCCCCCC[C@H]([C@H](CC[C@@H]([C@@H]1CC[C@H](O1)[C@H](CCCCCCCCCCC(CC1=CC(OC1=O)(C)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	656.49	Volume:	705.234 ? Van der Waals volume.
Dense:	0.931	LogP:	5.855 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.854 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.33 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	28.0	Rigid Bonds:	11.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	2.0
Heavy Atoms:	9.0

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:	4.948	Fsp³:	0.919
MCE-18:	38.535 ? 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:	0.633	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.426	Promiscuous compounds:	0.412

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.157	MDCK Permeability:	-4.839
Pgp-inhibitor:	0.0	Pgp-substrate:	0.321
PAMPA:	0.982 ? 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):	0.677
20% Bioavailability (F20%):	0.988	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.755
Plasma Protein Binding (PPB):	92.692%	Volume Distribution (VD):	0.511
Fu:	5.484% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.61
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.023
BSEP inhibitor:	0.284

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.025	CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
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):

4.934

Half-life (T1/2):

1.248

ADMET: Toxicity

hERG Blockers:	0.457	hERG Blockers (10um):	0.77
Human Hepatotoxicity (H-HT):	0.692	Drug-induced Liver Injury (DILI):	0.095
AMES Toxicity:	0.055	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.61	Skin Sensitization:	0.99
Carcinogencity:	0.151	Eye Corrosion:	0.002
Eye Irritation:	0.63	Respiratory Toxicity:	0.92
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.926
Hematotoxicity:	0.123	Drug-induced Nephrotoxicity:	0.899
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.861	Hek293 Cytotoxicity:	0.248
BCF:	1.399 ? 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:	5.046 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.175 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.016 ? 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
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346951]
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[12828457]

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	2

Activity Type	# Activity
Cell line	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
NPT91	Cell line	KB	Homo sapiens	ED50	=	1.0	10'-4 ug/ml	PMID[12762801]
NPT189	Cell line	Vero	Chlorocebus aethiops	ED50	=	1.0	10'-2 ug/ml	PMID[12762801]

In vivo activity

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

Experimental ADME

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

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC473904 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	17756
0.1-0.2	30198
0.2-0.3	1623
0.3-0.4	70
0.4-0.5	71
0.5-0.6	85
0.6-0.7	49
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	Natural Product ID
0.7692	Intermediate Similarity	NPC11456
0.6923	Remote Similarity	NPC134865
0.6923	Remote Similarity	NPC103523
0.6923	Remote Similarity	NPC488627
0.6923	Remote Similarity	NPC488631
0.6471	Remote Similarity	NPC606043
0.6429	Remote Similarity	NPC139418
0.6415	Remote Similarity	NPC232555
0.6415	Remote Similarity	NPC171174
0.6415	Remote Similarity	NPC114694
0.6415	Remote Similarity	NPC485248
0.6415	Remote Similarity	NPC142117
0.6415	Remote Similarity	NPC480249
0.6415	Remote Similarity	NPC485249
0.6415	Remote Similarity	NPC240695
0.6346	Remote Similarity	NPC107986
0.6346	Remote Similarity	NPC223871
0.6346	Remote Similarity	NPC231009
0.6346	Remote Similarity	NPC103284
0.6346	Remote Similarity	NPC110710
0.6346	Remote Similarity	NPC1083
0.6346	Remote Similarity	NPC82795
0.6346	Remote Similarity	NPC286338
0.6346	Remote Similarity	NPC603931
0.6346	Remote Similarity	NPC604237
0.6316	Remote Similarity	NPC231096
0.6316	Remote Similarity	NPC475581
0.6316	Remote Similarity	NPC62118
0.6316	Remote Similarity	NPC107717
0.6316	Remote Similarity	NPC488252
0.6296	Remote Similarity	NPC488632
0.6296	Remote Similarity	NPC477011
0.625	Remote Similarity	NPC329838
0.6226	Remote Similarity	NPC488253
0.6226	Remote Similarity	NPC473669
0.6226	Remote Similarity	NPC488251
0.6207	Remote Similarity	NPC233551
0.6207	Remote Similarity	NPC40376
0.6207	Remote Similarity	NPC21208
0.6182	Remote Similarity	NPC280621
0.6182	Remote Similarity	NPC48338
0.6182	Remote Similarity	NPC488628
0.614	Remote Similarity	NPC473478
0.614	Remote Similarity	NPC473651
0.614	Remote Similarity	NPC66346
0.6071	Remote Similarity	NPC478998
0.6034	Remote Similarity	NPC283085
0.6034	Remote Similarity	NPC132496
0.6034	Remote Similarity	NPC606740
0.6034	Remote Similarity	NPC608614
0.5965	Remote Similarity	NPC20621
0.5965	Remote Similarity	NPC318963
0.5965	Remote Similarity	NPC605101
0.5818	Remote Similarity	NPC81045
0.5818	Remote Similarity	NPC39754
0.5818	Remote Similarity	NPC171135
0.5818	Remote Similarity	NPC182383
0.5818	Remote Similarity	NPC61257
0.5818	Remote Similarity	NPC320569
0.5818	Remote Similarity	NPC133730
0.5818	Remote Similarity	NPC191929
0.5818	Remote Similarity	NPC100454
0.5818	Remote Similarity	NPC242364
0.5818	Remote Similarity	NPC172821
0.5818	Remote Similarity	NPC274446
0.5818	Remote Similarity	NPC485251
0.5818	Remote Similarity	NPC151403
0.5818	Remote Similarity	NPC261952
0.5818	Remote Similarity	NPC605171
0.5789	Remote Similarity	NPC178215
0.5789	Remote Similarity	NPC42598
0.5789	Remote Similarity	NPC473687
0.5789	Remote Similarity	NPC204686
0.5789	Remote Similarity	NPC219498
0.5789	Remote Similarity	NPC308412
0.5789	Remote Similarity	NPC134885
0.5789	Remote Similarity	NPC488247
0.5789	Remote Similarity	NPC210218
0.5789	Remote Similarity	NPC488248
0.5741	Remote Similarity	NPC329829
0.5738	Remote Similarity	NPC91067
0.5714	Remote Similarity	NPC93794
0.5714	Remote Similarity	NPC473504
0.5714	Remote Similarity	NPC81778
0.5714	Remote Similarity	NPC40066
0.5714	Remote Similarity	NPC47937
0.569	Remote Similarity	NPC488250
0.5593	Remote Similarity	NPC69082
0.5593	Remote Similarity	NPC488249
0.5536	Remote Similarity	NPC156804
0.55	Remote Similarity	NPC130359
0.55	Remote Similarity	NPC14901
0.5484	Remote Similarity	NPC480081
0.5455	Remote Similarity	NPC100921
0.5455	Remote Similarity	NPC475159
0.5455	Remote Similarity	NPC131002
0.5455	Remote Similarity	NPC473780
0.5455	Remote Similarity	NPC477018
0.5455	Remote Similarity	NPC604521
0.5424	Remote Similarity	NPC134807
0.5424	Remote Similarity	NPC602738
0.541	Remote Similarity	NPC488623
0.541	Remote Similarity	NPC488624
0.541	Remote Similarity	NPC488629
0.5385	Remote Similarity	NPC279267
0.5246	Remote Similarity	NPC169511
0.5246	Remote Similarity	NPC287164
0.5246	Remote Similarity	NPC234077
0.5238	Remote Similarity	NPC488630
0.5238	Remote Similarity	NPC488625
0.5238	Remote Similarity	NPC488626
0.5185	Remote Similarity	NPC73310
0.5185	Remote Similarity	NPC473529
0.5185	Remote Similarity	NPC180363
0.5185	Remote Similarity	NPC94875
0.5185	Remote Similarity	NPC11332
0.5185	Remote Similarity	NPC145914
0.5185	Remote Similarity	NPC601174
0.5185	Remote Similarity	NPC601403
0.5185	Remote Similarity	NPC603568
0.5185	Remote Similarity	NPC604330
0.5185	Remote Similarity	NPC608300
0.5185	Remote Similarity	NPC611200
0.5185	Remote Similarity	NPC611571
0.5172	Remote Similarity	NPC163093
0.5172	Remote Similarity	NPC600524
0.5172	Remote Similarity	NPC608355
0.5167	Remote Similarity	NPC329615
0.5091	Remote Similarity	NPC112685
0.5085	Remote Similarity	NPC219652
0.5085	Remote Similarity	NPC473840
0.5085	Remote Similarity	NPC480079
0.5082	Remote Similarity	NPC20339
0.5082	Remote Similarity	NPC477012
0.5079	Remote Similarity	NPC239517

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6662
0.1-0.2	2452
0.2-0.3	36
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