NPASS Compound

Natural Product: NPC157699

Natural Product ID	NPC157699
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XQNUUVURUCLCRZ-CJCKZRPTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	16109838
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 81 85 0 0 0 0 0 0 0 0999 V2000 7.2631 1.5654 3.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3043 0.6469 3.4583 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2146 0.3446 2.8235 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5471 1.1598 1.8371 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4076 0.8676 1.1491 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8404 -0.3310 1.4284 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4556 -1.1836 2.3921 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5417 -0.8995 3.0496 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0705 -1.7866 3.9884 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7072 -2.4245 2.5340 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5330 -2.6663 1.9622 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9215 1.7765 0.1068 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5993 1.7517 -0.2656 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2191 2.6741 -1.2320 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0089 2.7515 -1.6178 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1426 3.4956 -1.7499 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8101 4.3907 -2.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6486 5.2203 -3.3396 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9930 5.2528 -2.9897 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3856 4.3630 -1.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4458 3.5167 -1.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8290 2.6297 -0.4349 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7948 6.1276 -3.6515 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4073 4.3782 -3.1246 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5738 0.9217 0.1459 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1026 0.0200 -0.7336 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7258 -0.4288 -1.8854 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7407 -1.8516 -2.2291 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1884 -2.7261 -1.5298 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2313 -1.9927 -0.7419 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7965 -3.0340 0.2408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7606 -2.5751 1.0675 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8936 -2.0238 0.5838 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1313 -2.9060 0.7707 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1636 -2.1983 1.5954 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4699 -0.8069 1.1691 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2268 -0.1097 0.7103 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1778 1.2602 1.4094 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2768 2.0304 0.9781 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0913 -0.7716 1.1367 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4141 -0.8484 0.1232 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7885 -2.3238 2.9395 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6372 -3.2457 -0.4891 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7502 -0.9366 -0.0661 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8626 -3.6087 -2.4495 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0565 -2.3861 -2.2767 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4379 0.3303 -3.0529 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5072 1.8501 4.6999 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2536 1.2364 3.2101 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0236 2.5378 3.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0908 2.0984 1.7083 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9642 -0.6729 0.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5658 -2.6615 4.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7083 -2.0981 2.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2598 -3.7887 1.9675 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3370 -2.3842 0.8984 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2868 5.8683 -4.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4071 4.3706 -1.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4551 6.5972 -4.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1390 4.7618 -4.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8689 0.7233 -1.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7938 -0.1377 -1.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4490 -1.9009 -3.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3724 -3.4069 -0.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0281 -1.6265 -1.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9488 -3.4335 0.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1408 -3.9259 -0.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8069 -1.8915 -0.5303 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8473 -3.8230 1.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0993 -2.8321 1.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9627 -0.2097 1.9727 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2401 0.1106 -0.3550 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2565 1.1337 2.5261 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2730 1.8238 1.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6250 1.6281 0.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7005 -1.7963 -0.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8410 -2.1302 3.0338 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4372 -3.7838 -0.3648 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8504 -3.1649 -3.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2111 -2.9239 -1.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5601 0.4425 -2.9986 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 7 10 1 0 10 11 1 0 5 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 19 23 1 0 17 24 1 0 13 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 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 36 41 1 0 35 42 1 0 34 43 1 0 30 44 1 0 29 45 1 0 28 46 1 0 27 47 1 0 8 3 1 0 22 12 1 0 44 26 1 0 21 16 1 0 40 33 1 0 1 48 1 0 1 49 1 0 1 50 1 0 4 51 1 0 6 52 1 0 9 53 1 0 11 54 1 0 11 55 1 0 11 56 1 0 18 57 1 0 20 58 1 0 23 59 1 0 24 60 1 0 26 61 1 6 27 62 1 1 28 63 1 6 29 64 1 1 30 65 1 6 31 66 1 0 31 67 1 0 33 68 1 6 34 69 1 1 35 70 1 1 36 71 1 1 37 72 1 6 38 73 1 0 38 74 1 0 39 75 1 0 41 76 1 0 42 77 1 0 43 78 1 0 45 79 1 0 46 80 1 0 47 81 1 0 M END

Standard InCHIKey	XQNUUVURUCLCRZ-CJCKZRPTSA-N
Standard InCHI	InChI=1S/C29H34O18/c1-41-13-3-9(4-14(42-2)18(13)33)26-27(21(36)17-11(32)5-10(31)6-12(17)44-26)47-29-25(40)23(38)20(35)16(46-29)8-43-28-24(39)22(37)19(34)15(7-30)45-28/h3-6,15-16,19-20,22-25,28-35,37-40H,7-8H2,1-2H3/t15-,16-,19-,20-,22+,23+,24-,25-,28-,29+/m1/s1
SMILES	COc1cc(cc(c1O)OC)c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	670.17	Volume:	604.49 ? Van der Waals volume.
Dense:	1.109	LogP:	0.095 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.796 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.448 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	287.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.837	Fsp³:	0.483
MCE-18:	124.744 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.6	Fluc inhibitor:	0.159 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.783 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.606 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.06	Promiscuous compounds:	0.546

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.374	MDCK Permeability:	-5.393
Pgp-inhibitor:	0.001	Pgp-substrate:	0.535
PAMPA:	0.78 ? 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):	0.892
20% Bioavailability (F20%):	0.01	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.021
Plasma Protein Binding (PPB):	82.73%	Volume Distribution (VD):	-0.227
Fu:	14.362% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.983
BSEP inhibitor:	0.006

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.986
HLM stability:	0.097 ? 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):

1.49

Half-life (T1/2):

4.538

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.052
Human Hepatotoxicity (H-HT):	0.533	Drug-induced Liver Injury (DILI):	0.869
AMES Toxicity:	0.903	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.024	Skin Sensitization:	0.998
Carcinogencity:	0.1	Eye Corrosion:	0.0
Eye Irritation:	0.114	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.968
Hematotoxicity:	0.107	Drug-induced Nephrotoxicity:	0.387
Genotoxicity:	0.654	RPMI-8226 Immunitoxicity:	0.174
A549 Cytotoxicity:	0.531	Hek293 Cytotoxicity:	0.598
BCF:	0.328 ? 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:	2.994 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.537 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.603 ? 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
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711344]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19025748]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245240]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22351977]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO19826	Helicoverpa armigera	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2012	Turnera diffusa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26103	Streptomyces bobili	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2495	Agave xylonacantha	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6766	Antiphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9567	Enicosanthum cupulare	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10991	Maackia tashiroi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9136	Pseudocyclosorus subochthodes	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2012	Turnera diffusa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2495	Agave xylonacantha	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19826	Helicoverpa armigera	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26103	Streptomyces bobili	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6766	Antiphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9567	Enicosanthum cupulare	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10991	Maackia tashiroi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9136	Pseudocyclosorus subochthodes	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	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

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

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 NPC157699 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	22404
0.1-0.2	23068
0.2-0.3	3234
0.3-0.4	646
0.4-0.5	288
0.5-0.6	124
0.6-0.7	50
0.7-0.8	1
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8354	Intermediate Similarity	NPC325555
0.8354	Intermediate Similarity	NPC226304
0.8118	Intermediate Similarity	NPC156869
0.8095	Intermediate Similarity	NPC609888
0.7582	Intermediate Similarity	NPC476472
0.7582	Intermediate Similarity	NPC294815
0.7582	Intermediate Similarity	NPC16194
0.7363	Intermediate Similarity	NPC473327
0.7191	Intermediate Similarity	NPC173582
0.7191	Intermediate Similarity	NPC265885
0.7191	Intermediate Similarity	NPC181465
0.7191	Intermediate Similarity	NPC215710
0.7191	Intermediate Similarity	NPC39834
0.7191	Intermediate Similarity	NPC473438
0.7191	Intermediate Similarity	NPC253788
0.7126	Intermediate Similarity	NPC203050
0.7126	Intermediate Similarity	NPC225434
0.7111	Intermediate Similarity	NPC203259
0.7111	Intermediate Similarity	NPC33054
0.7111	Intermediate Similarity	NPC176740
0.7111	Intermediate Similarity	NPC471725
0.7111	Intermediate Similarity	NPC134532
0.7111	Intermediate Similarity	NPC602582
0.7079	Intermediate Similarity	NPC471079
0.701	Intermediate Similarity	NPC189564
0.7	Intermediate Similarity	NPC67326
0.6957	Remote Similarity	NPC488073
0.6957	Remote Similarity	NPC153755
0.6939	Remote Similarity	NPC292019
0.6939	Remote Similarity	NPC202908
0.6897	Remote Similarity	NPC120099
0.686	Remote Similarity	NPC472459
0.6706	Remote Similarity	NPC19388
0.6706	Remote Similarity	NPC240431
0.6706	Remote Similarity	NPC77672
0.6706	Remote Similarity	NPC55786
0.6706	Remote Similarity	NPC133671
0.6706	Remote Similarity	NPC135391
0.6706	Remote Similarity	NPC78263
0.6706	Remote Similarity	NPC250069
0.6628	Remote Similarity	NPC145038
0.6628	Remote Similarity	NPC56077
0.6628	Remote Similarity	NPC281131
0.6628	Remote Similarity	NPC64305
0.6628	Remote Similarity	NPC253662
0.6628	Remote Similarity	NPC179950
0.6628	Remote Similarity	NPC88789
0.6628	Remote Similarity	NPC491374
0.6591	Remote Similarity	NPC60735
0.6591	Remote Similarity	NPC26230
0.6566	Remote Similarity	NPC203145
0.6517	Remote Similarity	NPC609478
0.6484	Remote Similarity	NPC116864
0.6484	Remote Similarity	NPC244776
0.6449	Remote Similarity	NPC192539
0.6429	Remote Similarity	NPC292929
0.6364	Remote Similarity	NPC602448
0.6275	Remote Similarity	NPC219043
0.6275	Remote Similarity	NPC48984
0.6264	Remote Similarity	NPC223747
0.6238	Remote Similarity	NPC89052
0.6214	Remote Similarity	NPC217520
0.617	Remote Similarity	NPC29958
0.617	Remote Similarity	NPC139320
0.6162	Remote Similarity	NPC76831
0.6146	Remote Similarity	NPC473571
0.6146	Remote Similarity	NPC110941
0.6117	Remote Similarity	NPC173837
0.6105	Remote Similarity	NPC471748
0.6095	Remote Similarity	NPC139571
0.6082	Remote Similarity	NPC126784
0.6082	Remote Similarity	NPC241423
0.6082	Remote Similarity	NPC488074
0.6067	Remote Similarity	NPC265530
0.6044	Remote Similarity	NPC219904
0.6	Remote Similarity	NPC603655
0.5979	Remote Similarity	NPC129264
0.5977	Remote Similarity	NPC288084
0.5977	Remote Similarity	NPC34531
0.5962	Remote Similarity	NPC477895
0.5938	Remote Similarity	NPC470405
0.5918	Remote Similarity	NPC470125
0.5909	Remote Similarity	NPC67037
0.5909	Remote Similarity	NPC255615
0.5876	Remote Similarity	NPC65563
0.5876	Remote Similarity	NPC470949
0.587	Remote Similarity	NPC175107
0.5859	Remote Similarity	NPC12013
0.5859	Remote Similarity	NPC470443
0.5859	Remote Similarity	NPC11432
0.5859	Remote Similarity	NPC477613
0.5851	Remote Similarity	NPC170052
0.5851	Remote Similarity	NPC135846
0.5843	Remote Similarity	NPC111929
0.5843	Remote Similarity	NPC320283
0.5843	Remote Similarity	NPC135599
0.5843	Remote Similarity	NPC73855
0.5843	Remote Similarity	NPC41121
0.5843	Remote Similarity	NPC113968
0.5843	Remote Similarity	NPC328940
0.5843	Remote Similarity	NPC277174
0.5843	Remote Similarity	NPC606877
0.5842	Remote Similarity	NPC85751
0.5842	Remote Similarity	NPC471669
0.5842	Remote Similarity	NPC19240
0.5842	Remote Similarity	NPC220173
0.5833	Remote Similarity	NPC187379
0.5816	Remote Similarity	NPC186816
0.5806	Remote Similarity	NPC101026
0.5806	Remote Similarity	NPC488077
0.58	Remote Similarity	NPC122467
0.58	Remote Similarity	NPC37668
0.58	Remote Similarity	NPC270448
0.5789	Remote Similarity	NPC254855
0.5789	Remote Similarity	NPC94610
0.5784	Remote Similarity	NPC287889
0.5778	Remote Similarity	NPC127546
0.5778	Remote Similarity	NPC57625
0.5778	Remote Similarity	NPC173637
0.5778	Remote Similarity	NPC317489
0.5778	Remote Similarity	NPC223424
0.5778	Remote Similarity	NPC600591
0.5728	Remote Similarity	NPC223426
0.5714	Remote Similarity	NPC304741
0.5686	Remote Similarity	NPC89127
0.5673	Remote Similarity	NPC214621
0.5673	Remote Similarity	NPC34267
0.5673	Remote Similarity	NPC81042
0.5657	Remote Similarity	NPC255157
0.5657	Remote Similarity	NPC259896
0.5652	Remote Similarity	NPC488080
0.5652	Remote Similarity	NPC169977
0.5638	Remote Similarity	NPC197285
0.5631	Remote Similarity	NPC470449
0.5631	Remote Similarity	NPC221342
0.5631	Remote Similarity	NPC476470
0.5612	Remote Similarity	NPC275454
0.5591	Remote Similarity	NPC42773
0.5591	Remote Similarity	NPC21100
0.5591	Remote Similarity	NPC45522
0.5579	Remote Similarity	NPC206123
0.5577	Remote Similarity	NPC470446
0.5556	Remote Similarity	NPC277532
0.5556	Remote Similarity	NPC605592
0.5506	Remote Similarity	NPC54802
0.5506	Remote Similarity	NPC197304
0.5478	Remote Similarity	NPC25946
0.5474	Remote Similarity	NPC601710
0.547	Remote Similarity	NPC473554
0.5463	Remote Similarity	NPC25523
0.5463	Remote Similarity	NPC303694
0.5455	Remote Similarity	NPC163242
0.5455	Remote Similarity	NPC272068
0.5444	Remote Similarity	NPC276222
0.5444	Remote Similarity	NPC274618
0.5444	Remote Similarity	NPC118284
0.5444	Remote Similarity	NPC608147
0.5431	Remote Similarity	NPC21359
0.5431	Remote Similarity	NPC460984
0.5426	Remote Similarity	NPC599850
0.5422	Remote Similarity	NPC189589
0.5417	Remote Similarity	NPC88023
0.5417	Remote Similarity	NPC209023
0.5417	Remote Similarity	NPC309025
0.54	Remote Similarity	NPC155877
0.5376	Remote Similarity	NPC297987
0.5368	Remote Similarity	NPC191306
0.5361	Remote Similarity	NPC488072
0.5357	Remote Similarity	NPC208769
0.5357	Remote Similarity	NPC470713
0.5327	Remote Similarity	NPC121703
0.5321	Remote Similarity	NPC480441
0.5319	Remote Similarity	NPC24043
0.5294	Remote Similarity	NPC296018
0.5294	Remote Similarity	NPC154741
0.5269	Remote Similarity	NPC289667
0.5269	Remote Similarity	NPC143851
0.5263	Remote Similarity	NPC222936
0.5248	Remote Similarity	NPC102028
0.5238	Remote Similarity	NPC470447
0.5238	Remote Similarity	NPC473073
0.5225	Remote Similarity	NPC470718
0.5217	Remote Similarity	NPC241781
0.5213	Remote Similarity	NPC8573
0.5213	Remote Similarity	NPC136042
0.5208	Remote Similarity	NPC159579
0.5208	Remote Similarity	NPC182121
0.5208	Remote Similarity	NPC488071
0.5189	Remote Similarity	NPC470445
0.5182	Remote Similarity	NPC470712
0.5172	Remote Similarity	NPC37074
0.5169	Remote Similarity	NPC78697
0.5161	Remote Similarity	NPC476771
0.5158	Remote Similarity	NPC84362
0.5155	Remote Similarity	NPC224530
0.513	Remote Similarity	NPC488079
0.5114	Remote Similarity	NPC287780
0.5114	Remote Similarity	NPC60982
0.5102	Remote Similarity	NPC116458
0.5102	Remote Similarity	NPC246943

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC157699 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5911
0.1-0.2	3176
0.2-0.3	51
0.3-0.4	5
0.4-0.5	4
0.5-0.6	2
0.6-0.7	0
0.7-0.8	1
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
0.7111	Intermediate Similarity	NPD6797	Phase 2
0.5534	Remote Similarity	NPD7251	Phase 2
0.5472	Remote Similarity	NPD7808	Phase 3

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