NPASS Compound

Natural Product: NPC79765

Natural Product ID	NPC79765
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OUJDQONJYHNTDX-UMUUNPGWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	91431845
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid 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 72 76 0 0 0 0 0 0 0 0999 V2000 2.4383 1.5867 1.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8036 1.6418 1.6112 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5901 0.9759 0.6485 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8970 0.2853 -0.3108 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 0.2407 -0.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7385 0.8934 0.6052 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2832 0.8671 0.5994 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4985 1.9897 0.7769 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8061 1.9521 0.7643 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4824 0.8195 0.5780 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8508 0.7953 0.5669 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5952 -0.3878 0.3721 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8423 -1.5196 0.1934 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4422 -1.5011 0.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7557 -0.3322 0.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3782 -0.3242 0.4039 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3009 -1.3741 0.2381 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7430 -2.6618 0.0202 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9670 -0.3228 0.3751 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8176 -1.3851 0.2040 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7483 -1.6123 1.3826 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6856 -0.4430 1.5788 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7755 0.3377 0.2705 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7942 -0.7046 -0.8293 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1427 -0.0199 -2.1583 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3985 0.5347 -2.1263 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5335 -1.2128 -0.9817 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9379 1.1064 0.2944 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3463 0.3553 2.6415 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4311 -2.8025 1.1490 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9593 1.0641 0.7375 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8453 0.4662 -0.1366 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6976 1.5131 -0.8560 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3649 0.7314 -1.9942 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8218 -0.6109 -1.5373 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7495 -0.8781 -0.0810 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0570 -0.5882 0.6388 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1435 -1.1547 -0.0197 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7391 -0.2939 0.6202 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2285 -1.6628 -2.2715 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3064 1.4710 -2.6635 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8203 2.4614 -1.3708 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8462 2.1094 2.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3225 2.1879 2.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4538 -0.2435 -1.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0495 -0.3235 -1.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0012 2.9360 0.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4091 1.7032 0.7103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3544 -2.4798 0.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9465 -3.2964 -0.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2652 -2.3285 0.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1063 -1.7665 2.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6974 -0.8580 1.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8947 0.9676 0.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5639 -1.4537 -0.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3352 0.7431 -2.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0203 -0.8020 -2.9354 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2783 1.5248 -2.0546 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2902 1.1452 1.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3688 0.3894 2.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6649 -3.2871 1.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3387 -0.1053 -0.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4568 1.9444 -0.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5162 0.5490 -2.7196 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9163 -0.6798 -1.8200 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6137 -1.9960 0.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9470 -1.0018 1.6631 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1438 0.5119 0.7432 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8938 -0.4944 0.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5879 -1.3072 -2.9217 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7732 2.0368 -1.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0290 3.3785 -1.0648 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 14 18 1 0 12 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 24 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 3 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 36 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 6 1 1 0 16 7 1 0 27 20 1 0 39 32 1 0 15 10 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 8 47 1 0 11 48 1 0 13 49 1 0 18 50 1 0 20 51 1 6 21 52 1 1 22 53 1 1 23 54 1 6 24 55 1 1 25 56 1 0 25 57 1 0 26 58 1 0 28 59 1 0 29 60 1 0 30 61 1 0 32 62 1 6 33 63 1 1 34 64 1 6 35 65 1 6 36 66 1 6 37 67 1 0 37 68 1 0 38 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	OUJDQONJYHNTDX-UMUUNPGWSA-N
Standard InCHI	InChI=1S/C27H30O15/c28-7-16-20(32)22(34)24(36)26(41-16)39-11-3-1-10(2-4-11)13-9-38-15-6-12(5-14(30)18(15)19(13)31)40-27-25(37)23(35)21(33)17(8-29)42-27/h1-6,9,16-17,20-30,32-37H,7-8H2/t16-,17-,20-,21-,22+,23+,24-,25-,26-,27-/m1/s1
SMILES	c1cc(ccc1c1coc2cc(cc(c2c1=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.277 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.127 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.89 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.598	Fsp³:	0.444
MCE-18:	115.923 ? 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:	0.611	Fluc inhibitor:	0.294 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.913 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.575 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.309	Promiscuous compounds:	0.401

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.785	MDCK Permeability:	-4.917
Pgp-inhibitor:	0.0	Pgp-substrate:	0.355
PAMPA:	1.0 ? 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):	0.989
20% Bioavailability (F20%):	0.057	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.007
Plasma Protein Binding (PPB):	77.58%	Volume Distribution (VD):	-0.296
Fu:	21.39% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.064
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.067
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):

1.656

Half-life (T1/2):

5.262

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.862	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	0.999
Carcinogencity:	0.136	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.39	Drug-induced Nephrotoxicity:	0.97
Genotoxicity:	0.93	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.425	Hek293 Cytotoxicity:	0.18
BCF:	0.438 ? 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:	3.101 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.779 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.745 ? 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
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2020.112278]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043426]
NPO4886	Coniochaeta saccardoi	Species	Coniochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21082806]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21574561]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747095]
NPO3866	Pistia stratiotes	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24258601]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29192771]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30792999]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36080366]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36359928]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37898811]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38267697]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38744893]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39592251]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	indopacific	n.a.	PMID[9917317]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21102	Thalictrum wangii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3866	Pistia stratiotes	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2502	Lupinus mexicanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22983	Calicotome villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Shoot Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21102	Thalictrum wangii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2502	Lupinus mexicanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16529	Plagiodera versicolora	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3866	Pistia stratiotes	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10255	Ipomoea muricata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21685	Magnolia coco	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21982	Erechtites hieraciifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4886	Coniochaeta saccardoi	Species	Coniochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24195	Stylissa carteri	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12511	Leplaea thompsonii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22983	Calicotome villosa	Species	Fabaceae	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 NPC79765 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	20803
0.1-0.2	25211
0.2-0.3	2651
0.3-0.4	848
0.4-0.5	259
0.5-0.6	52
0.6-0.7	23
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC73511
0.8696	High Similarity	NPC197896
0.8696	High Similarity	NPC313163
0.8429	Intermediate Similarity	NPC234739
0.8406	Intermediate Similarity	NPC160515
0.7917	Intermediate Similarity	NPC156457
0.76	Intermediate Similarity	NPC80140
0.7342	Intermediate Similarity	NPC487212
0.7297	Intermediate Similarity	NPC348541
0.7284	Intermediate Similarity	NPC479405
0.7195	Intermediate Similarity	NPC479404
0.6974	Remote Similarity	NPC258035
0.6933	Remote Similarity	NPC45165
0.6795	Remote Similarity	NPC205076
0.6795	Remote Similarity	NPC138540
0.6753	Remote Similarity	NPC487213
0.6753	Remote Similarity	NPC161749
0.675	Remote Similarity	NPC307518
0.6711	Remote Similarity	NPC135345
0.6623	Remote Similarity	NPC289667
0.65	Remote Similarity	NPC224462
0.6437	Remote Similarity	NPC479403
0.642	Remote Similarity	NPC229729
0.6375	Remote Similarity	NPC100720
0.6329	Remote Similarity	NPC95090
0.6329	Remote Similarity	NPC27408
0.6296	Remote Similarity	NPC479402
0.6279	Remote Similarity	NPC303913
0.6265	Remote Similarity	NPC48773
0.6176	Remote Similarity	NPC116632
0.6125	Remote Similarity	NPC105511
0.6104	Remote Similarity	NPC25547
0.6098	Remote Similarity	NPC481043
0.6024	Remote Similarity	NPC601607
0.5926	Remote Similarity	NPC603782
0.5921	Remote Similarity	NPC191154
0.5904	Remote Similarity	NPC479401
0.5904	Remote Similarity	NPC285197
0.5882	Remote Similarity	NPC479407
0.5844	Remote Similarity	NPC134819
0.5833	Remote Similarity	NPC22832
0.5833	Remote Similarity	NPC243930
0.5833	Remote Similarity	NPC610187
0.5802	Remote Similarity	NPC39360
0.5802	Remote Similarity	NPC29763
0.5802	Remote Similarity	NPC210003
0.5732	Remote Similarity	NPC297987
0.5732	Remote Similarity	NPC277205
0.5732	Remote Similarity	NPC37919
0.5732	Remote Similarity	NPC136042
0.5732	Remote Similarity	NPC323593
0.5732	Remote Similarity	NPC203500
0.5732	Remote Similarity	NPC189142
0.5732	Remote Similarity	NPC77660
0.5663	Remote Similarity	NPC84362
0.5647	Remote Similarity	NPC486578
0.561	Remote Similarity	NPC261866
0.561	Remote Similarity	NPC211014
0.5595	Remote Similarity	NPC60966
0.5581	Remote Similarity	NPC479406
0.5581	Remote Similarity	NPC607707
0.5568	Remote Similarity	NPC251417
0.5529	Remote Similarity	NPC307938
0.5526	Remote Similarity	NPC203636
0.5465	Remote Similarity	NPC601144
0.5422	Remote Similarity	NPC58053
0.5422	Remote Similarity	NPC143851
0.5417	Remote Similarity	NPC303644
0.5402	Remote Similarity	NPC116458
0.5402	Remote Similarity	NPC246943
0.5402	Remote Similarity	NPC311830
0.5402	Remote Similarity	NPC605784
0.5385	Remote Similarity	NPC249824
0.5385	Remote Similarity	NPC133400
0.5357	Remote Similarity	NPC64305
0.5294	Remote Similarity	NPC22195
0.5294	Remote Similarity	NPC186807
0.5294	Remote Similarity	NPC21190
0.5269	Remote Similarity	NPC64425
0.5227	Remote Similarity	NPC607201
0.5169	Remote Similarity	NPC267254
0.5169	Remote Similarity	NPC601586
0.5116	Remote Similarity	NPC181712
0.5059	Remote Similarity	NPC259070
0.5057	Remote Similarity	NPC472459
0.5049	Remote Similarity	NPC470716

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC79765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4790
0.1-0.2	4258
0.2-0.3	86
0.3-0.4	10
0.4-0.5	5
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
0.6753	Remote Similarity	NPD4381	Clinical (unspecified phase)

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