NPASS Compound

Natural Product: NPC197980

Natural Product ID	NPC197980
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TYEFCPJCPSRVMT-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46173975
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

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 100105 0 0 0 0 0 0 0 0999 V2000 0.4622 -3.3074 0.0428 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0744 -1.9349 0.0867 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0605 -1.0156 0.4140 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3713 -1.3868 0.6908 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3387 -0.4622 1.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9600 0.8600 1.0557 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6676 1.2489 0.7849 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7022 0.3159 0.4607 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6653 0.7290 0.1720 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0897 1.0396 -1.0914 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3937 1.4250 -1.2968 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3070 1.5112 -0.2556 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6833 1.9415 -0.5204 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6271 0.8500 -0.8831 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1749 0.1307 -2.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2612 -0.8190 -1.6631 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4542 -1.0734 -0.3185 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7806 -1.8380 0.3908 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6148 -0.2672 0.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8219 -1.1745 -0.0079 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1066 -0.5168 0.1625 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6843 -0.3936 1.3985 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9139 0.2299 1.5601 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5674 0.7358 0.4541 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0024 0.6201 -0.7880 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7725 -0.0074 -0.9249 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6455 1.1203 -1.8969 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0635 0.9974 -3.1684 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8140 1.3738 0.5775 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5162 0.3632 2.8142 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8773 -0.1394 3.9482 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8603 1.1945 1.0068 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5551 0.8076 1.2205 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1444 0.4929 2.5326 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0841 0.5876 3.5715 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7023 -0.8940 1.2961 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6075 -0.9424 0.1062 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1542 -1.8667 -0.9777 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9637 -1.4115 -2.0797 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0979 -0.0335 -1.9804 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4271 0.7294 -2.9201 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7890 0.3656 -0.5978 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7978 1.2770 0.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1553 0.7440 0.1330 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0579 0.9543 -0.8947 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3608 0.4718 -0.8639 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7689 -0.2488 0.2435 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8659 -0.4611 1.2763 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5743 0.0181 1.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3318 -1.1923 2.3642 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5282 -1.4793 3.4733 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0579 -0.7411 0.3024 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2486 0.6971 -1.9105 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7944 1.4370 -3.0231 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2675 -3.4079 -0.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4226 -3.9447 -0.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8092 -3.6254 1.0691 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5871 -2.4443 0.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6615 1.6612 1.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3703 2.3099 0.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3827 0.9742 -1.9073 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6954 1.6696 -2.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1178 2.5491 0.3031 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6298 2.6351 -1.4135 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6469 1.2817 -1.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8175 0.7859 -2.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0755 -0.4556 -2.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4964 0.0964 1.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8090 -1.6451 -1.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6603 -2.0267 0.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2108 -0.7744 2.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3769 -0.0715 -1.9321 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8476 1.3209 -3.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7906 -0.0762 -3.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1320 1.5844 -3.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6577 0.9342 0.2387 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3653 0.2881 4.8688 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8062 0.1840 3.9952 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8814 -1.2533 4.0183 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5464 1.2513 1.8705 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5318 1.6124 3.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6527 0.3318 4.5592 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9045 -0.1694 3.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7535 -1.8758 1.8077 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1764 -0.1640 2.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6203 -1.2990 0.4172 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4503 -2.9259 -0.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1053 -1.7743 -1.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8415 0.9550 -0.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4418 1.5360 1.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8345 2.1969 -0.5802 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7588 1.5173 -1.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8866 -0.1510 2.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5186 -0.6437 4.2140 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0302 -2.3329 4.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5190 -1.7538 3.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3288 -1.4972 -0.3156 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6056 1.4663 -3.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8823 1.0159 -3.4709 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5702 2.4923 -2.7643 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 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 24 29 1 0 23 30 1 0 30 31 1 0 12 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 5 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 1 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 48 50 1 0 50 51 1 0 47 52 1 0 46 53 1 0 53 54 1 0 8 3 1 0 33 9 1 0 42 37 1 0 49 44 1 0 19 14 1 0 26 21 1 0 1 55 1 0 1 56 1 0 1 57 1 0 4 58 1 0 6 59 1 0 7 60 1 0 10 61 1 0 11 62 1 0 13 63 1 0 13 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 19 68 1 0 20 69 1 0 20 70 1 0 22 71 1 0 26 72 1 0 28 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 37 86 1 0 38 87 1 0 38 88 1 0 42 89 1 0 43 90 1 0 43 91 1 0 45 92 1 0 49 93 1 0 51 94 1 0 51 95 1 0 51 96 1 0 52 97 1 0 54 98 1 0 54 99 1 0 54100 1 0 M END

Standard InCHIKey	TYEFCPJCPSRVMT-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C42H46O12/c1-47-33-15-23(11-27-21-53-41(45)31(27)13-25-17-35(49-3)39(43)36(18-25)50-4)7-9-29(33)30-10-8-24(16-34(30)48-2)12-28-22-54-42(46)32(28)14-26-19-37(51-5)40(44)38(20-26)52-6/h7-10,15-20,27-28,31-32,43-44H,11-14,21-22H2,1-6H3
SMILES	COc1cc(ccc1c1ccc(CC2COC(=O)C2Cc2cc(c(c(c2)OC)O)OC)cc1OC)CC1COC(=O)C1Cc1cc(c(c(c1)OC)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	742.3	Volume:	752.221 ? Van der Waals volume.
Dense:	0.987	LogP:	2.841 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.75 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.972 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	36.0
TPSA:	148.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.245	Fsp³:	0.381
MCE-18:	121.862 ? 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:	0.991	Fluc inhibitor:	0.095 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.527 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.236	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.307	MDCK Permeability:	-4.832
Pgp-inhibitor:	0.916	Pgp-substrate:	0.005
PAMPA:	0.0 ? 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):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	99.427%	Volume Distribution (VD):	-0.523
Fu:	0.377% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.852	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.993 ? 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):

2.986

Half-life (T1/2):

1.991

ADMET: Toxicity

hERG Blockers:	0.92	hERG Blockers (10um):	0.943
Human Hepatotoxicity (H-HT):	0.995	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.321	Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	0.808
Carcinogencity:	0.815	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.199
Drug-induced Neurotoxicity:	0.52	Ototoxicity:	0.999
Hematotoxicity:	0.887	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.961	RPMI-8226 Immunitoxicity:	0.516
A549 Cytotoxicity:	0.958	Hek293 Cytotoxicity:	0.984
BCF:	1.371 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.112 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.528 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.059 ? 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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1111/ppl.12252]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10449	Arctium lappa	Species	Asteraceae	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 NPC197980 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	18019
0.1-0.2	28292
0.2-0.3	3308
0.3-0.4	168
0.4-0.5	42
0.5-0.6	22
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7321	Intermediate Similarity	NPC273657
0.6721	Remote Similarity	NPC145569
0.6607	Remote Similarity	NPC68779
0.6607	Remote Similarity	NPC108598
0.65	Remote Similarity	NPC106920
0.65	Remote Similarity	NPC15811
0.6393	Remote Similarity	NPC293757
0.6393	Remote Similarity	NPC668
0.597	Remote Similarity	NPC478705
0.5968	Remote Similarity	NPC300776
0.5968	Remote Similarity	NPC176814
0.5968	Remote Similarity	NPC4982
0.5968	Remote Similarity	NPC606629
0.5926	Remote Similarity	NPC72796
0.5862	Remote Similarity	NPC211386
0.5714	Remote Similarity	NPC223807
0.5714	Remote Similarity	NPC5310
0.5672	Remote Similarity	NPC216223
0.5522	Remote Similarity	NPC282291
0.5522	Remote Similarity	NPC166137
0.5429	Remote Similarity	NPC478703
0.5429	Remote Similarity	NPC478704
0.5397	Remote Similarity	NPC176586
0.5397	Remote Similarity	NPC210354
0.5246	Remote Similarity	NPC40237
0.5217	Remote Similarity	NPC174512
0.5082	Remote Similarity	NPC92693
0.5079	Remote Similarity	NPC205915
0.5077	Remote Similarity	NPC191158
0.5077	Remote Similarity	NPC177644

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC197980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3566
0.1-0.2	5463
0.2-0.3	120
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data