NPASS Compound

Natural Product: NPC202340

Natural Product ID	NPC202340
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GWLRHJMIGLBHRL-DOOHVXTOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101781231
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 93 98 0 0 0 0 0 0 0 0999 V2000 6.1487 -1.5590 -3.1300 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2972 -2.8056 -3.1061 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8281 -3.8055 -2.1333 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8880 -4.1096 -0.9869 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1442 -2.8996 -0.5029 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7517 -1.9584 -1.6077 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4064 -1.6059 -1.5362 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2409 -0.2307 -1.3696 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7480 0.0196 -1.3062 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0224 -0.4262 -2.5306 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0229 0.5999 -2.8769 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7688 1.0948 -1.6341 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7432 1.6755 -0.7334 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5577 1.3877 -1.1370 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0086 3.0658 -0.5910 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9761 3.6815 0.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1290 3.5228 1.4516 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1158 2.8701 1.0429 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1265 4.1129 2.6928 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2127 4.0145 3.5558 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1701 4.6256 4.8086 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0583 5.3355 5.2151 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0077 5.4113 4.3387 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0055 4.8155 3.0750 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0226 4.9223 2.2875 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1075 4.3843 1.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3318 4.6051 0.3030 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5225 4.3600 -1.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7365 4.5732 -1.6749 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8140 5.0571 -0.9741 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6543 5.3169 0.3672 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4418 5.0971 0.9960 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0541 5.2830 -1.6089 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0316 5.9428 6.4732 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3320 3.3061 3.1602 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5781 0.0876 -1.0965 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9803 0.1619 -1.1264 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4746 1.1792 -1.6595 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8137 -0.8997 -0.5638 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3069 -1.9681 0.0041 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0412 -3.0608 0.5814 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4335 -3.1190 0.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0951 -4.2078 1.1680 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4024 -5.2395 1.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0052 -5.1981 1.7479 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3876 -4.1012 1.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3398 -6.2431 2.3309 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9278 -6.2397 2.3539 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0753 -6.3060 2.3130 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3295 1.7259 -3.3743 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5191 -1.6962 -2.3236 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9545 -2.5128 -2.8697 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8389 -2.2416 0.5367 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6815 -4.5612 0.0658 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0555 -5.0412 -2.7841 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3473 -1.1486 -2.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7299 -0.7928 -3.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1399 -1.8482 -3.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3383 -3.2370 -4.1272 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8251 -3.4681 -1.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1927 -4.9399 -1.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1936 -3.2698 -0.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3599 -1.0328 -1.5102 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7214 0.1138 -0.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7303 0.3358 -2.1741 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3801 -0.5614 -0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7926 -0.5047 -3.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 0.2201 -3.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4359 1.8893 -2.0132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8159 1.1721 0.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0342 4.5195 5.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1144 5.9552 4.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 4.0078 -1.6195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8531 4.3657 -2.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5125 5.6985 0.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3530 5.3090 2.0383 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6035 6.1262 -1.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3427 6.6738 6.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2066 3.8466 3.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8839 -0.8013 -0.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2083 -1.9988 0.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9977 -2.3238 0.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1777 -4.2392 1.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2932 -4.0934 1.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5433 -7.2291 2.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6314 -5.4960 3.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4916 -5.9499 1.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0265 -6.2593 2.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7571 2.0889 -4.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0458 -2.3829 -2.8718 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1890 -1.6334 0.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1760 -4.4804 0.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7083 -4.8304 -3.4932 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 22 34 1 0 20 35 1 0 12 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 1 0 44 49 1 0 11 50 1 0 10 51 1 0 6 52 1 0 5 53 1 0 4 54 1 0 3 55 1 0 52 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 46 41 1 0 24 19 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 6 3 60 1 1 4 61 1 6 5 62 1 1 6 63 1 6 8 64 1 0 8 65 1 0 9 66 1 1 10 67 1 6 11 68 1 6 12 69 1 6 13 70 1 1 21 71 1 0 23 72 1 0 28 73 1 0 29 74 1 0 31 75 1 0 32 76 1 0 33 77 1 0 34 78 1 0 35 79 1 0 39 80 1 0 40 81 1 0 42 82 1 0 43 83 1 0 46 84 1 0 48 85 1 0 48 86 1 0 48 87 1 0 49 88 1 0 50 89 1 0 51 90 1 0 53 91 1 0 54 92 1 0 55 93 1 0 M END

Standard InCHIKey	GWLRHJMIGLBHRL-DOOHVXTOSA-N
Standard InCHI	InChI=1S/C37H38O18/c1-15-27(43)30(46)32(48)36(51-15)50-14-24-28(44)31(47)35(54-25(42)10-4-16-3-9-20(40)22(11-16)49-2)37(53-24)55-34-29(45)26-21(41)12-19(39)13-23(26)52-33(34)17-5-7-18(38)8-6-17/h3-13,15,24,27-28,30-32,35-41,43-44,46-48H,14H2,1-2H3/b10-4+/t15-,24+,27-,28+,30+,31-,32+,35+,36+,37-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(cc2)O)O)O)OC(=O)/C=C/c2ccc(c(c2)OC)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.21	Volume:	721.119 ? Van der Waals volume.
Dense:	1.068	LogP:	1.162 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.364 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.881 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	38.0
TPSA:	284.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.079	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.053	Fsp³:	0.351
MCE-18:	139.4 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.726	Fluc inhibitor:	0.646 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.824 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.703 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.184	Promiscuous compounds:	0.447

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.268	MDCK Permeability:	-5.353
Pgp-inhibitor:	0.001	Pgp-substrate:	0.707
PAMPA:	0.992 ? 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):	0.018
20% Bioavailability (F20%):	0.614	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.027
Plasma Protein Binding (PPB):	86.743%	Volume Distribution (VD):	-0.048
Fu:	10.184% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.919
BSEP inhibitor:	0.595

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.036
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.45
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.84 ? 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):

0.94

Half-life (T1/2):

3.965

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.254
Human Hepatotoxicity (H-HT):	0.432	Drug-induced Liver Injury (DILI):	0.824
AMES Toxicity:	0.841	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.178	Skin Sensitization:	0.998
Carcinogencity:	0.058	Eye Corrosion:	0.0
Eye Irritation:	0.2	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.842
Hematotoxicity:	0.019	Drug-induced Nephrotoxicity:	0.238
Genotoxicity:	0.96	RPMI-8226 Immunitoxicity:	0.191
A549 Cytotoxicity:	0.737	Hek293 Cytotoxicity:	0.927
BCF:	0.698 ? 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:	3.495 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.752 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.18 ? 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
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	bud covers	n.a.	n.a.	PMID[11975520]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[12662107]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16643051]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[16989517]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3839140]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7684040]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9868153]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO875	Cryptocarya oblata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12386	Russula japonica	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2469	Erythrophleum couminga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7608	Phelline lucida	Species	Phellinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7731	Lactuca serriola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13192	Chara ceratophylla	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16013	Inga velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12726	Piptostigma fugax	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12035	Rhododendron ungerni	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14274	Rhododendron mucronatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20585	Urochloa decumbens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16306	Curcuma caesia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13683	Cosmos diversifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9342	Solenopsis punctaticeps	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO206	Ormosia nobilis	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1398	Trichodesma incanum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11046	Ocimum pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5870	Xenia florida	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10892	Xanthorrhoea resinosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10594	Centaurea solstitialis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5380	Eucalyptus australiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12207	Lagochilus leiacanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14075	Streptomyces viridogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14379	Onobrychis viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10928	Xenia obscuronata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3059	Erythrina pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2046	Cathormion altissimum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12557	Strychnos tricalysioides	Species	Loganiaceae	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 NPC202340 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	15404
0.1-0.2	29802
0.2-0.3	3706
0.3-0.4	534
0.4-0.5	223
0.5-0.6	101
0.6-0.7	69
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8476	Intermediate Similarity	NPC162394
0.8036	Intermediate Similarity	NPC473554
0.7797	Intermediate Similarity	NPC487501
0.7642	Intermediate Similarity	NPC173837
0.7456	Intermediate Similarity	NPC25946
0.7451	Intermediate Similarity	NPC12013
0.7451	Intermediate Similarity	NPC11432
0.7451	Intermediate Similarity	NPC477613
0.7429	Intermediate Similarity	NPC218161
0.729	Intermediate Similarity	NPC89052
0.7238	Intermediate Similarity	NPC89127
0.717	Intermediate Similarity	NPC221342
0.717	Intermediate Similarity	NPC476470
0.7167	Intermediate Similarity	NPC249560
0.7131	Intermediate Similarity	NPC487500
0.7103	Intermediate Similarity	NPC602448
0.7083	Intermediate Similarity	NPC487502
0.708	Intermediate Similarity	NPC470713
0.6975	Remote Similarity	NPC231787
0.6949	Remote Similarity	NPC21359
0.6949	Remote Similarity	NPC460984
0.6887	Remote Similarity	NPC122467
0.686	Remote Similarity	NPC72554
0.6833	Remote Similarity	NPC275977
0.6752	Remote Similarity	NPC241781
0.6724	Remote Similarity	NPC474522
0.664	Remote Similarity	NPC97817
0.6585	Remote Similarity	NPC30011
0.6581	Remote Similarity	NPC156785
0.6571	Remote Similarity	NPC173582
0.6571	Remote Similarity	NPC265885
0.6571	Remote Similarity	NPC181465
0.6571	Remote Similarity	NPC215710
0.6571	Remote Similarity	NPC473438
0.6571	Remote Similarity	NPC253788
0.6514	Remote Similarity	NPC142142
0.6455	Remote Similarity	NPC476472
0.6455	Remote Similarity	NPC294815
0.6455	Remote Similarity	NPC16194
0.6441	Remote Similarity	NPC470717
0.6422	Remote Similarity	NPC473327
0.641	Remote Similarity	NPC474093
0.641	Remote Similarity	NPC104910
0.6396	Remote Similarity	NPC292929
0.6387	Remote Similarity	NPC470720
0.6379	Remote Similarity	NPC470718
0.6364	Remote Similarity	NPC221288
0.6364	Remote Similarity	NPC194836
0.6364	Remote Similarity	NPC91493
0.6364	Remote Similarity	NPC605081
0.6356	Remote Similarity	NPC480445
0.6348	Remote Similarity	NPC470712
0.6348	Remote Similarity	NPC303694
0.6346	Remote Similarity	NPC476215
0.6306	Remote Similarity	NPC85751
0.6306	Remote Similarity	NPC19240
0.6281	Remote Similarity	NPC192539
0.6207	Remote Similarity	NPC217520
0.6195	Remote Similarity	NPC483767
0.6195	Remote Similarity	NPC483769
0.6195	Remote Similarity	NPC483768
0.6195	Remote Similarity	NPC483766
0.6174	Remote Similarity	NPC470416
0.614	Remote Similarity	NPC214621
0.614	Remote Similarity	NPC34267
0.614	Remote Similarity	NPC483765
0.6117	Remote Similarity	NPC216496
0.6111	Remote Similarity	NPC163242
0.6111	Remote Similarity	NPC272068
0.608	Remote Similarity	NPC487499
0.6071	Remote Similarity	NPC101399
0.6071	Remote Similarity	NPC217822
0.6071	Remote Similarity	NPC11847
0.6071	Remote Similarity	NPC198938
0.6055	Remote Similarity	NPC203259
0.6055	Remote Similarity	NPC33054
0.6055	Remote Similarity	NPC176740
0.6055	Remote Similarity	NPC471725
0.6055	Remote Similarity	NPC134532
0.6055	Remote Similarity	NPC602582
0.6018	Remote Similarity	NPC220173
0.6	Remote Similarity	NPC488734
0.6	Remote Similarity	NPC295625
0.6	Remote Similarity	NPC488735
0.6	Remote Similarity	NPC488739
0.6	Remote Similarity	NPC488732
0.6	Remote Similarity	NPC488738
0.5984	Remote Similarity	NPC480444
0.5983	Remote Similarity	NPC477895
0.5982	Remote Similarity	NPC104883
0.5982	Remote Similarity	NPC488679
0.597	Remote Similarity	NPC33083
0.5966	Remote Similarity	NPC139571
0.5913	Remote Similarity	NPC223426
0.5902	Remote Similarity	NPC470719
0.5856	Remote Similarity	NPC473571
0.5856	Remote Similarity	NPC110941
0.5833	Remote Similarity	NPC95866
0.5826	Remote Similarity	NPC260504
0.5826	Remote Similarity	NPC89809
0.5812	Remote Similarity	NPC203145
0.5806	Remote Similarity	NPC488737
0.5798	Remote Similarity	NPC25523
0.5727	Remote Similarity	NPC471079
0.5726	Remote Similarity	NPC478277
0.5726	Remote Similarity	NPC96605
0.5726	Remote Similarity	NPC280642
0.5726	Remote Similarity	NPC478276
0.5726	Remote Similarity	NPC478275
0.5726	Remote Similarity	NPC92815
0.5726	Remote Similarity	NPC81042
0.5701	Remote Similarity	NPC224530
0.568	Remote Similarity	NPC209550
0.5676	Remote Similarity	NPC39834
0.5667	Remote Similarity	NPC164704
0.5664	Remote Similarity	NPC470125
0.5652	Remote Similarity	NPC603079
0.5645	Remote Similarity	NPC488740
0.5645	Remote Similarity	NPC488736
0.5645	Remote Similarity	NPC488733
0.5635	Remote Similarity	NPC480443
0.5625	Remote Similarity	NPC155877
0.5625	Remote Similarity	NPC304741
0.5596	Remote Similarity	NPC170052
0.5596	Remote Similarity	NPC135846
0.5577	Remote Similarity	NPC111929
0.5577	Remote Similarity	NPC320283
0.5577	Remote Similarity	NPC41121
0.5556	Remote Similarity	NPC36138
0.5526	Remote Similarity	NPC153755
0.5517	Remote Similarity	NPC205824
0.5505	Remote Similarity	NPC223747
0.55	Remote Similarity	NPC189564
0.5487	Remote Similarity	NPC65563
0.5487	Remote Similarity	NPC470949
0.5463	Remote Similarity	NPC219904
0.5441	Remote Similarity	NPC475179
0.5439	Remote Similarity	NPC129264
0.5439	Remote Similarity	NPC470444
0.5439	Remote Similarity	NPC186816
0.541	Remote Similarity	NPC470715
0.5398	Remote Similarity	NPC470405
0.5391	Remote Similarity	NPC126784
0.5391	Remote Similarity	NPC240306
0.5391	Remote Similarity	NPC241423
0.5385	Remote Similarity	NPC480470
0.5351	Remote Similarity	NPC156869
0.5339	Remote Similarity	NPC470447
0.5285	Remote Similarity	NPC480441
0.5273	Remote Similarity	NPC259957
0.5263	Remote Similarity	NPC67326
0.5254	Remote Similarity	NPC97119
0.5231	Remote Similarity	NPC480442
0.5231	Remote Similarity	NPC480472
0.5214	Remote Similarity	NPC477628
0.5203	Remote Similarity	NPC219043
0.5203	Remote Similarity	NPC480796
0.5182	Remote Similarity	NPC48093
0.5175	Remote Similarity	NPC187379
0.5172	Remote Similarity	NPC255157
0.5172	Remote Similarity	NPC35167
0.5172	Remote Similarity	NPC259896
0.5169	Remote Similarity	NPC139060
0.5169	Remote Similarity	NPC270448
0.5167	Remote Similarity	NPC470449
0.5133	Remote Similarity	NPC254855
0.5133	Remote Similarity	NPC116864
0.5133	Remote Similarity	NPC244776
0.5133	Remote Similarity	NPC94610
0.5128	Remote Similarity	NPC61904
0.5116	Remote Similarity	NPC488078
0.5106	Remote Similarity	NPC482521
0.5093	Remote Similarity	NPC127546
0.5093	Remote Similarity	NPC57625
0.5093	Remote Similarity	NPC173637
0.5093	Remote Similarity	NPC317489
0.5093	Remote Similarity	NPC223424
0.5093	Remote Similarity	NPC600591
0.5085	Remote Similarity	NPC470443
0.5083	Remote Similarity	NPC76831
0.5083	Remote Similarity	NPC477629
0.5081	Remote Similarity	NPC292019
0.5081	Remote Similarity	NPC48984
0.5081	Remote Similarity	NPC202908
0.5081	Remote Similarity	NPC472993
0.5046	Remote Similarity	NPC265530
0.5045	Remote Similarity	NPC159579
0.5043	Remote Similarity	NPC609888

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC202340 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4422
0.1-0.2	4657
0.2-0.3	62
0.3-0.4	4
0.4-0.5	4
0.5-0.6	0
0.6-0.7	1
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
0.6055	Remote Similarity	NPD6797	Phase 2

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