NPASS Compound

Natural Product: NPC231644

Natural Product ID	NPC231644
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UMLQYKKIQCBBDM-XYSSDXFWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101036025
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 73 77 0 0 0 0 0 0 0 0999 V2000 -3.4592 -2.7265 -0.1127 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1841 -2.4391 -1.5736 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4274 -1.9190 -2.2422 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1681 -0.8998 -3.3008 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3105 0.2208 -2.7602 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4608 -0.2471 -1.5958 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0971 -1.5862 -1.7355 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2986 0.4932 -1.4753 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2827 1.1629 -0.2914 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3312 2.6634 -0.6720 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9189 3.4533 0.5369 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2835 2.6824 1.7632 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9809 3.4806 3.0388 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6283 1.4817 1.8980 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1429 1.0049 0.6146 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2880 -0.3163 0.9243 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5993 -0.4906 1.4016 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7411 -0.3486 2.7875 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7303 -0.0939 3.4965 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9793 -0.4893 3.3505 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1347 -0.3487 4.7304 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3779 -0.4878 5.3019 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4507 -0.7680 4.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2908 -0.9051 3.1125 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0337 -0.7668 2.5142 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8758 -0.8957 1.2307 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6778 -0.7650 0.6535 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 -0.9360 -0.7808 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5068 -1.1461 -1.5126 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5549 -1.2434 -2.8898 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7400 -1.1353 -3.5749 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8966 -0.9256 -2.8606 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8281 -0.8310 -1.4921 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1210 -0.8116 -3.5239 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7929 -1.2338 -4.9784 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3654 -1.4579 -3.6081 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7295 -0.9194 4.9899 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0041 -0.0660 5.5050 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6431 4.6461 0.5384 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3977 2.8389 -1.6896 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1598 1.2619 -2.3901 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3994 -0.3835 -3.7092 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1647 -2.9589 -2.8287 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4272 -3.8079 0.1300 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7046 -2.2335 0.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4969 -2.3838 0.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9198 -3.4027 -2.0558 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1140 -1.4455 -1.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6630 -1.3909 -4.1776 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6840 0.5950 -3.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0742 -0.0919 -0.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2168 0.9214 0.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3590 2.9451 -0.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1806 3.6453 0.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3998 2.5493 1.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0270 2.7225 3.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0614 3.8415 3.0293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7303 4.2410 3.2446 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7139 1.6814 0.4476 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5289 -0.3843 6.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1103 -1.1251 2.4266 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5387 -1.2791 -1.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7788 -0.6619 -0.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8454 -0.2810 -3.0549 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5181 -0.8226 -5.5168 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2173 -0.8150 -4.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8091 -1.1232 5.9776 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3756 -0.8542 5.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2152 4.7489 1.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6043 2.3194 -2.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1055 1.3347 -1.4038 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1414 -0.7086 -3.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4192 -3.5821 -2.1118 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 31 35 1 0 30 36 1 0 23 37 1 0 21 38 1 0 11 39 1 0 10 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 7 2 1 0 15 9 1 0 27 17 2 0 33 28 1 0 25 20 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 1 4 49 1 6 5 50 1 6 6 51 1 1 9 52 1 1 10 53 1 6 11 54 1 6 12 55 1 6 13 56 1 0 13 57 1 0 13 58 1 0 15 59 1 6 22 60 1 0 24 61 1 0 29 62 1 0 33 63 1 0 34 64 1 0 35 65 1 0 36 66 1 0 37 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	UMLQYKKIQCBBDM-XYSSDXFWSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-7-16(32)20(36)22(38)26(39-7)43-25-21(37)17(33)8(2)40-27(25)42-24-19(35)15-11(29)5-10(28)6-14(15)41-23(24)9-3-12(30)18(34)13(31)4-9/h3-8,16-17,20-22,25-34,36-38H,1-2H3/t7-,8-,16-,17-,20+,21+,22+,25+,26-,27-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1cc(c(c(c1)O)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	1.114 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.493 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.45 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.886	Fsp³:	0.444
MCE-18:	126.462 ? 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:	1
Colloidal aggregators:	0.64	Fluc inhibitor:	0.184 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.847 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.596 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.312	Promiscuous compounds:	0.874

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.36	MDCK Permeability:	-4.954
Pgp-inhibitor:	0.0	Pgp-substrate:	0.869
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):	0.57
20% Bioavailability (F20%):	0.793	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.124
Plasma Protein Binding (PPB):	81.618%	Volume Distribution (VD):	-0.1
Fu:	15.999% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.982
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.678
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.928 ? 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):

1.936

Half-life (T1/2):

5.01

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.604
Human Hepatotoxicity (H-HT):	0.388	Drug-induced Liver Injury (DILI):	0.962
AMES Toxicity:	0.824	Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.216	Skin Sensitization:	1.0
Carcinogencity:	0.036	Eye Corrosion:	0.0
Eye Irritation:	0.888	Respiratory Toxicity:	0.041
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.982
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.045
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.965	Hek293 Cytotoxicity:	0.489
BCF:	0.47 ? 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:	3.124 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.674 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.883 ? 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
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22791	Astraeus pteridis	Species	Astraeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19067555]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29726697]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34443694]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34770961]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35631245]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37020229]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37226152]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257205]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38381096]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38695450]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39407547]
NPO23494	Centaurea linifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5054	Limonium gmelinii	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4594	Vitellaria paradoxa	Species	Sapotaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4594	Vitellaria paradoxa	Species	Sapotaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5054	Limonium gmelinii	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5054	Limonium gmelinii	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5054	Limonium gmelinii	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23494	Centaurea linifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21956	Alyxia reinwardtii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23879	Serratula inermis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4594	Vitellaria paradoxa	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20604	Cneoridium dumosum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25848	Oscillochloris trichoides	Species	Oscillochloridaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5054	Limonium gmelinii	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22791	Astraeus pteridis	Species	Astraeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24327	Machilus macrantha	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23954	Tridachia crispata	n.a.	n.a.	n.a.	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 NPC231644 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	22514
0.1-0.2	24179
0.2-0.3	2422
0.3-0.4	381
0.4-0.5	154
0.5-0.6	118
0.6-0.7	61
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8816	High Similarity	NPC95866
0.8442	Intermediate Similarity	NPC476215
0.7927	Intermediate Similarity	NPC155877
0.7632	Intermediate Similarity	NPC135599
0.7632	Intermediate Similarity	NPC73855
0.7632	Intermediate Similarity	NPC113968
0.7632	Intermediate Similarity	NPC328940
0.7632	Intermediate Similarity	NPC277174
0.7632	Intermediate Similarity	NPC606877
0.759	Intermediate Similarity	NPC163242
0.759	Intermediate Similarity	NPC272068
0.7558	Intermediate Similarity	NPC122467
0.7262	Intermediate Similarity	NPC258044
0.7262	Intermediate Similarity	NPC217387
0.7241	Intermediate Similarity	NPC12013
0.7241	Intermediate Similarity	NPC11432
0.7241	Intermediate Similarity	NPC477613
0.7229	Intermediate Similarity	NPC254855
0.7229	Intermediate Similarity	NPC94610
0.7176	Intermediate Similarity	NPC39834
0.7	Intermediate Similarity	NPC220173
0.6905	Remote Similarity	NPC170052
0.6905	Remote Similarity	NPC135846
0.6848	Remote Similarity	NPC602448
0.6813	Remote Similarity	NPC89127
0.6739	Remote Similarity	NPC221342
0.6739	Remote Similarity	NPC476470
0.6702	Remote Similarity	NPC89052
0.6667	Remote Similarity	NPC127546
0.6667	Remote Similarity	NPC19388
0.6667	Remote Similarity	NPC240431
0.6667	Remote Similarity	NPC57625
0.6667	Remote Similarity	NPC55786
0.6667	Remote Similarity	NPC173637
0.6667	Remote Similarity	NPC317489
0.6667	Remote Similarity	NPC223424
0.6667	Remote Similarity	NPC303694
0.6667	Remote Similarity	NPC600591
0.6629	Remote Similarity	NPC35167
0.6627	Remote Similarity	NPC216496
0.6517	Remote Similarity	NPC605592
0.65	Remote Similarity	NPC34531
0.6471	Remote Similarity	NPC484158
0.6444	Remote Similarity	NPC255157
0.6444	Remote Similarity	NPC259896
0.6436	Remote Similarity	NPC488740
0.6436	Remote Similarity	NPC488736
0.6436	Remote Similarity	NPC488733
0.6386	Remote Similarity	NPC265530
0.6373	Remote Similarity	NPC480444
0.6341	Remote Similarity	NPC111929
0.6341	Remote Similarity	NPC320283
0.6341	Remote Similarity	NPC41121
0.6333	Remote Similarity	NPC203259
0.6333	Remote Similarity	NPC33054
0.6333	Remote Similarity	NPC176740
0.6333	Remote Similarity	NPC471725
0.6333	Remote Similarity	NPC134532
0.6333	Remote Similarity	NPC602582
0.6311	Remote Similarity	NPC488737
0.6238	Remote Similarity	NPC488734
0.6238	Remote Similarity	NPC488735
0.6238	Remote Similarity	NPC488739
0.6238	Remote Similarity	NPC488732
0.6238	Remote Similarity	NPC488738
0.6222	Remote Similarity	NPC470405
0.6176	Remote Similarity	NPC480445
0.6163	Remote Similarity	NPC182121
0.6163	Remote Similarity	NPC219904
0.6154	Remote Similarity	NPC304741
0.6145	Remote Similarity	NPC476771
0.6087	Remote Similarity	NPC470444
0.6071	Remote Similarity	NPC476772
0.6064	Remote Similarity	NPC482026
0.6061	Remote Similarity	NPC173837
0.6044	Remote Similarity	NPC173582
0.6044	Remote Similarity	NPC265885
0.6044	Remote Similarity	NPC181465
0.6044	Remote Similarity	NPC215710
0.6044	Remote Similarity	NPC473438
0.6044	Remote Similarity	NPC253788
0.6022	Remote Similarity	NPC240306
0.5962	Remote Similarity	NPC162394
0.5938	Remote Similarity	NPC76831
0.5895	Remote Similarity	NPC32641
0.5895	Remote Similarity	NPC256188
0.5895	Remote Similarity	NPC473327
0.5876	Remote Similarity	NPC292929
0.5872	Remote Similarity	NPC487499
0.587	Remote Similarity	NPC471748
0.5862	Remote Similarity	NPC138927
0.5843	Remote Similarity	NPC223747
0.5833	Remote Similarity	NPC142142
0.5814	Remote Similarity	NPC145038
0.5814	Remote Similarity	NPC56077
0.5814	Remote Similarity	NPC281131
0.5814	Remote Similarity	NPC253662
0.5814	Remote Similarity	NPC179950
0.5814	Remote Similarity	NPC158674
0.5814	Remote Similarity	NPC88789
0.5814	Remote Similarity	NPC491374
0.5794	Remote Similarity	NPC192539
0.5773	Remote Similarity	NPC473071
0.5761	Remote Similarity	NPC29958
0.573	Remote Similarity	NPC189913
0.573	Remote Similarity	NPC224530
0.5729	Remote Similarity	NPC35119
0.5699	Remote Similarity	NPC267680
0.5684	Remote Similarity	NPC253521
0.5684	Remote Similarity	NPC113836
0.5676	Remote Similarity	NPC473554
0.5664	Remote Similarity	NPC487502
0.5647	Remote Similarity	NPC67037
0.5647	Remote Similarity	NPC255615
0.5632	Remote Similarity	NPC64305
0.5618	Remote Similarity	NPC175107
0.5612	Remote Similarity	NPC476472
0.5612	Remote Similarity	NPC294815
0.5612	Remote Similarity	NPC16194
0.5591	Remote Similarity	NPC139320
0.5588	Remote Similarity	NPC219043
0.5588	Remote Similarity	NPC48984
0.5575	Remote Similarity	NPC30011
0.5545	Remote Similarity	NPC203145
0.5543	Remote Similarity	NPC116864
0.5543	Remote Similarity	NPC244776
0.5534	Remote Similarity	NPC480441
0.5532	Remote Similarity	NPC196127
0.5532	Remote Similarity	NPC67326
0.5521	Remote Similarity	NPC61904
0.5517	Remote Similarity	NPC77672
0.5517	Remote Similarity	NPC133671
0.5517	Remote Similarity	NPC135391
0.5517	Remote Similarity	NPC78263
0.5517	Remote Similarity	NPC250069
0.551	Remote Similarity	NPC97119
0.5506	Remote Similarity	NPC472459
0.5495	Remote Similarity	NPC136761
0.5474	Remote Similarity	NPC156869
0.547	Remote Similarity	NPC487500
0.5455	Remote Similarity	NPC471669
0.5446	Remote Similarity	NPC14187
0.5444	Remote Similarity	NPC60735
0.5444	Remote Similarity	NPC26230
0.5444	Remote Similarity	NPC48093
0.5437	Remote Similarity	NPC292019
0.5437	Remote Similarity	NPC202908
0.5424	Remote Similarity	NPC487501
0.5398	Remote Similarity	NPC231787
0.5393	Remote Similarity	NPC52550
0.5393	Remote Similarity	NPC349108
0.5385	Remote Similarity	NPC25523
0.5385	Remote Similarity	NPC120099
0.5385	Remote Similarity	NPC259957
0.537	Remote Similarity	NPC156785
0.5357	Remote Similarity	NPC21359
0.5357	Remote Similarity	NPC460984
0.5354	Remote Similarity	NPC603079
0.5349	Remote Similarity	NPC288084
0.5349	Remote Similarity	NPC276222
0.5349	Remote Similarity	NPC274618
0.5349	Remote Similarity	NPC118284
0.5349	Remote Similarity	NPC608147
0.5333	Remote Similarity	NPC325555
0.5333	Remote Similarity	NPC226304
0.5315	Remote Similarity	NPC480442
0.5263	Remote Similarity	NPC471079
0.5258	Remote Similarity	NPC115674
0.5258	Remote Similarity	NPC144097
0.5253	Remote Similarity	NPC37668
0.5222	Remote Similarity	NPC305811
0.5217	Remote Similarity	NPC609478
0.5214	Remote Similarity	NPC249560
0.5192	Remote Similarity	NPC189564
0.5172	Remote Similarity	NPC72554
0.5161	Remote Similarity	NPC209023
0.5158	Remote Similarity	NPC473682
0.5155	Remote Similarity	NPC65563
0.5155	Remote Similarity	NPC470949
0.5152	Remote Similarity	NPC483414
0.5135	Remote Similarity	NPC209550
0.5135	Remote Similarity	NPC241781
0.5133	Remote Similarity	NPC25946
0.513	Remote Similarity	NPC275977
0.5109	Remote Similarity	NPC235260
0.5109	Remote Similarity	NPC159579
0.5109	Remote Similarity	NPC155763
0.5106	Remote Similarity	NPC203050
0.5106	Remote Similarity	NPC225434
0.5106	Remote Similarity	NPC355481
0.5104	Remote Similarity	NPC187379
0.5104	Remote Similarity	NPC609888
0.51	Remote Similarity	NPC270448
0.5091	Remote Similarity	NPC474522
0.5089	Remote Similarity	NPC480443
0.5057	Remote Similarity	NPC54802
0.5057	Remote Similarity	NPC197304
0.5055	Remote Similarity	NPC271692
0.5051	Remote Similarity	NPC126784
0.5051	Remote Similarity	NPC241423

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC231644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5977
0.1-0.2	3133
0.2-0.3	32
0.3-0.4	5
0.4-0.5	2
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
0.6333	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