NPASS Compound

Natural Product: NPC319716

Natural Product ID	NPC319716
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OBVNUYXMOLOYPW-FIRGGUJXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21550297
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 114121 0 0 0 0 0 0 0 0999 V2000 11.6178 -0.8396 -0.3248 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1354 -0.4685 1.0397 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2124 0.7330 0.9542 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9379 0.3821 1.6528 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3339 -0.8677 1.0647 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8045 -0.6084 -0.3615 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6619 0.2224 -0.0865 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1875 -0.2644 1.2862 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1355 -1.1683 1.7128 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8288 -0.9004 1.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6243 -0.8666 -0.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4731 0.2654 -0.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8107 1.6207 -0.7770 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3621 1.5784 -0.3994 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5965 0.4705 -1.0428 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2130 -0.8574 -0.8925 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4292 -1.8287 -0.0139 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0251 -1.8703 -0.4445 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4225 -0.6825 -0.7056 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1402 0.5794 -0.5642 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4945 1.6950 -1.3237 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9055 1.5632 -1.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7271 0.5324 -0.9975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9932 -0.7843 -1.1214 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9172 0.4160 -1.7257 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0568 0.5837 -0.9478 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9399 -0.6685 -1.0136 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0745 -0.3094 -1.9262 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9353 0.6933 -1.1796 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0152 1.8382 -0.8130 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7451 1.7151 -1.3658 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8810 2.0413 0.6758 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1299 3.2137 0.8962 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4168 0.1621 0.0118 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7817 0.1592 0.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3066 -1.2429 0.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9177 -1.5765 1.5091 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9171 -0.5532 1.9393 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6478 0.7806 1.3085 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2924 0.9653 1.1141 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1297 1.8581 2.2570 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4343 1.7335 3.4706 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2208 -0.9259 1.6259 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6180 -2.7862 1.3251 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2124 -1.4807 -0.8734 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7894 -1.3978 -2.3769 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2121 -1.7620 -1.4688 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1439 1.0541 0.9030 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7497 0.1015 -2.4273 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6652 -1.9436 -0.9635 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2096 -1.9145 1.0691 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4335 -1.6734 1.6367 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0063 -0.3170 -1.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6658 -0.4987 -0.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5562 -1.9348 -0.4931 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9974 -0.2527 1.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6662 1.6069 1.5045 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0616 1.0622 -0.0922 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2272 1.1998 1.7403 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2146 0.1039 2.7081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5723 -0.0397 -0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0294 1.2774 0.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1340 0.5461 2.0240 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1029 -0.3548 1.6465 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8168 -1.9550 1.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0926 -1.8096 -0.8358 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3201 2.2271 0.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9446 2.2573 -1.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9041 2.5384 -0.7926 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2334 1.6671 0.6993 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5495 0.7606 -2.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1878 -1.3576 -1.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6064 -1.7019 1.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8759 -2.8407 -0.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5042 -2.7993 -0.5456 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6334 2.6844 -0.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0997 1.8644 -2.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9614 1.2666 -2.8270 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4101 2.5655 -1.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8987 0.7416 0.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0539 -1.1451 -2.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5270 -1.5954 -0.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6952 0.7745 0.0819 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3481 -0.8551 -0.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6342 0.2266 -2.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7817 1.0286 -1.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4440 2.8008 -1.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3517 1.2254 1.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8716 2.2440 1.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1110 3.4617 1.8464 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1568 0.6135 -0.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4414 -1.9432 0.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1335 -1.7834 2.2580 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8840 -0.4236 3.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2051 0.9271 0.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2295 1.8331 2.4052 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7903 2.8319 1.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0133 1.3656 4.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5857 -1.5457 2.2860 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1241 -2.6673 0.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9715 -2.3295 -1.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0640 -1.2228 -3.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9396 -1.5549 -2.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8229 0.4913 1.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1209 0.8551 1.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2687 2.1514 0.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2993 -0.8535 -2.7958 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8081 0.2254 -2.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2163 0.8926 -3.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7187 -2.3479 -1.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2059 -2.0225 -1.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2338 -2.6811 -0.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4100 -1.6457 2.7457 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0890 -2.5561 1.3750 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 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 28 46 1 0 27 47 1 0 20 48 1 0 12 49 1 0 6 50 1 0 5 51 1 0 51 52 1 0 52 2 1 0 9 5 1 0 12 7 1 0 16 11 1 0 20 15 1 0 24 19 1 0 31 26 1 0 40 35 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 0 3 57 1 0 3 58 1 0 4 59 1 0 4 60 1 0 6 61 1 0 7 62 1 0 8 63 1 0 10 64 1 0 10 65 1 0 11 66 1 0 13 67 1 0 13 68 1 0 14 69 1 0 14 70 1 0 15 71 1 0 16 72 1 0 17 73 1 0 17 74 1 0 18 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 23 80 1 0 24 81 1 0 24 82 1 0 26 83 1 0 27 84 1 0 28 85 1 0 29 86 1 0 30 87 1 0 32 88 1 0 32 89 1 0 33 90 1 0 35 91 1 0 36 92 1 0 37 93 1 0 38 94 1 0 39 95 1 0 41 96 1 0 41 97 1 0 42 98 1 0 43 99 1 0 44100 1 0 45101 1 0 46102 1 0 47103 1 0 48104 1 0 48105 1 0 48106 1 0 49107 1 0 49108 1 0 49109 1 0 50110 1 0 50111 1 0 50112 1 0 52113 1 0 52114 1 0 M END

Standard InCHIKey	OBVNUYXMOLOYPW-FIRGGUJXSA-N
Standard InCHI	InChI=1S/C39H62O13/c1-18-7-12-39(47-17-18)19(2)28-25(52-39)14-24-22-6-5-20-13-21(8-10-37(20,3)23(22)9-11-38(24,28)4)48-35-33(46)31(44)34(27(16-41)50-35)51-36-32(45)30(43)29(42)26(15-40)49-36/h5,18-19,21-36,40-46H,6-17H2,1-4H3/t18?,19?,21-,22?,23?,24?,25?,26+,27+,28?,29+,30+,31-,32+,33+,34+,35+,36-,37-,38-,39?/m0/s1
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)O)O)O)C)C)C)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	738.42	Volume:	726.285 ? Van der Waals volume.
Dense:	1.017	LogP:	1.549 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.597 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.348 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	42.0
TPSA:	196.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.193	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.216	Fsp³:	0.949
MCE-18:	198.421 ? 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:	0.013	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.169 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.214	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.533	MDCK Permeability:	-4.97
Pgp-inhibitor:	0.0	Pgp-substrate:	0.664
PAMPA:	0.991 ? 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):	0.498
20% Bioavailability (F20%):	0.151	30% Bioavailability (F30%):	0.935
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.293	MRP1:	1.0
Plasma Protein Binding (PPB):	57.87%	Volume Distribution (VD):	-0.409
Fu:	36.843% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.118	BCRP inhibitor:	0.006
BSEP inhibitor:	0.712

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.993	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.008
HLM stability:	0.006 ? 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):

1.564

Half-life (T1/2):

2.314

ADMET: Toxicity

hERG Blockers:	0.155	hERG Blockers (10um):	0.549
Human Hepatotoxicity (H-HT):	0.621	Drug-induced Liver Injury (DILI):	0.32
AMES Toxicity:	0.329	Rat Oral Acute Toxicity:	0.359
Maximum Recommended Daily Dose:	0.652	Skin Sensitization:	0.023
Carcinogencity:	0.148	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.021
Drug-induced Neurotoxicity:	0.521	Ototoxicity:	0.999
Hematotoxicity:	0.015	Drug-induced Nephrotoxicity:	0.022
Genotoxicity:	0.006	RPMI-8226 Immunitoxicity:	0.154
A549 Cytotoxicity:	0.075	Hek293 Cytotoxicity:	0.827
BCF:	1.568 ? 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:	4.076 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.755 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.663 ? 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
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30479	Dioscorea batatas	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30479	Dioscorea batatas	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30479	Dioscorea batatas	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27509	Dioscorea zingiberensis	Species	Dioscoreaceae	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 NPC319716 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	22820
0.1-0.2	23023
0.2-0.3	3171
0.3-0.4	572
0.4-0.5	121
0.5-0.6	84
0.6-0.7	35
0.7-0.8	1
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9176	High Similarity	NPC470432
0.9176	High Similarity	NPC230507
0.9012	High Similarity	NPC181845
0.8989	High Similarity	NPC477809
0.8478	Intermediate Similarity	NPC6806
0.8265	Intermediate Similarity	NPC477811
0.8	Intermediate Similarity	NPC480555
0.8	Intermediate Similarity	NPC150372
0.7938	Intermediate Similarity	NPC475550
0.7708	Intermediate Similarity	NPC300557
0.7684	Intermediate Similarity	NPC470433
0.7684	Intermediate Similarity	NPC46190
0.7684	Intermediate Similarity	NPC171073
0.7614	Intermediate Similarity	NPC325828
0.7576	Intermediate Similarity	NPC269297
0.7576	Intermediate Similarity	NPC222202
0.7553	Intermediate Similarity	NPC113044
0.7553	Intermediate Similarity	NPC283829
0.7553	Intermediate Similarity	NPC14704
0.7553	Intermediate Similarity	NPC161676
0.75	Intermediate Similarity	NPC602423
0.7379	Intermediate Similarity	NPC480553
0.7347	Intermediate Similarity	NPC249553
0.7184	Intermediate Similarity	NPC480554
0.7157	Intermediate Similarity	NPC475333
0.7157	Intermediate Similarity	NPC224098
0.7157	Intermediate Similarity	NPC208383
0.7143	Intermediate Similarity	NPC31896
0.7087	Intermediate Similarity	NPC194207
0.7087	Intermediate Similarity	NPC22779
0.7071	Intermediate Similarity	NPC248746
0.6909	Remote Similarity	NPC477808
0.6875	Remote Similarity	NPC107962
0.6827	Remote Similarity	NPC309278
0.6818	Remote Similarity	NPC224314
0.6759	Remote Similarity	NPC232054
0.6727	Remote Similarity	NPC480556
0.6696	Remote Similarity	NPC210569
0.6667	Remote Similarity	NPC42171
0.6667	Remote Similarity	NPC32361
0.6667	Remote Similarity	NPC182900
0.6667	Remote Similarity	NPC477807
0.6632	Remote Similarity	NPC250393
0.6522	Remote Similarity	NPC305771
0.6522	Remote Similarity	NPC94072
0.6522	Remote Similarity	NPC169816
0.6495	Remote Similarity	NPC107188
0.6381	Remote Similarity	NPC97700
0.6381	Remote Similarity	NPC184617
0.6381	Remote Similarity	NPC30856
0.6322	Remote Similarity	NPC100451
0.6277	Remote Similarity	NPC485594
0.6261	Remote Similarity	NPC15918
0.6204	Remote Similarity	NPC13193
0.6139	Remote Similarity	NPC15249
0.6139	Remote Similarity	NPC25455
0.6139	Remote Similarity	NPC6295
0.6102	Remote Similarity	NPC263359
0.6092	Remote Similarity	NPC235126
0.6092	Remote Similarity	NPC242419
0.6082	Remote Similarity	NPC234352
0.6078	Remote Similarity	NPC141433
0.6061	Remote Similarity	NPC206003
0.6061	Remote Similarity	NPC121453
0.6061	Remote Similarity	NPC473610
0.6019	Remote Similarity	NPC305423
0.5982	Remote Similarity	NPC132080
0.5979	Remote Similarity	NPC297348
0.5979	Remote Similarity	NPC249204
0.5979	Remote Similarity	NPC48339
0.5979	Remote Similarity	NPC141769
0.5979	Remote Similarity	NPC477547
0.5943	Remote Similarity	NPC92890
0.5914	Remote Similarity	NPC277715
0.5842	Remote Similarity	NPC19400
0.5833	Remote Similarity	NPC244431
0.5833	Remote Similarity	NPC486114
0.5818	Remote Similarity	NPC247037
0.578	Remote Similarity	NPC73243
0.578	Remote Similarity	NPC244086
0.578	Remote Similarity	NPC84956
0.5766	Remote Similarity	NPC475625
0.5766	Remote Similarity	NPC116756
0.5755	Remote Similarity	NPC161738
0.5752	Remote Similarity	NPC23808
0.5752	Remote Similarity	NPC87998
0.5727	Remote Similarity	NPC115165
0.5714	Remote Similarity	NPC232037
0.5714	Remote Similarity	NPC160426
0.57	Remote Similarity	NPC477451
0.5688	Remote Similarity	NPC475182
0.5686	Remote Similarity	NPC306131
0.5686	Remote Similarity	NPC211354
0.5686	Remote Similarity	NPC200802
0.5673	Remote Similarity	NPC94272
0.5673	Remote Similarity	NPC485595
0.5664	Remote Similarity	NPC470864
0.566	Remote Similarity	NPC475351
0.5625	Remote Similarity	NPC473518
0.5619	Remote Similarity	NPC195297
0.5614	Remote Similarity	NPC476112
0.5614	Remote Similarity	NPC83137
0.5614	Remote Similarity	NPC307534
0.5604	Remote Similarity	NPC486119
0.5596	Remote Similarity	NPC124677
0.5583	Remote Similarity	NPC79900
0.5567	Remote Similarity	NPC24960
0.5565	Remote Similarity	NPC233433
0.5543	Remote Similarity	NPC22140
0.5543	Remote Similarity	NPC243728
0.5543	Remote Similarity	NPC158088
0.5526	Remote Similarity	NPC249265
0.5517	Remote Similarity	NPC308140
0.5495	Remote Similarity	NPC102016
0.5495	Remote Similarity	NPC95051
0.5463	Remote Similarity	NPC42482
0.5463	Remote Similarity	NPC98696
0.5463	Remote Similarity	NPC40440
0.5446	Remote Similarity	NPC294686
0.5426	Remote Similarity	NPC282669
0.5424	Remote Similarity	NPC470866
0.5405	Remote Similarity	NPC128572
0.5377	Remote Similarity	NPC125324
0.5347	Remote Similarity	NPC177834
0.5339	Remote Similarity	NPC167183
0.5327	Remote Similarity	NPC70204
0.5283	Remote Similarity	NPC295980
0.5268	Remote Similarity	NPC150057
0.5268	Remote Similarity	NPC147753
0.5259	Remote Similarity	NPC218571
0.5259	Remote Similarity	NPC487615
0.5246	Remote Similarity	NPC220836
0.5225	Remote Similarity	NPC122819
0.5221	Remote Similarity	NPC294129
0.52	Remote Similarity	NPC296686
0.5192	Remote Similarity	NPC222731
0.5182	Remote Similarity	NPC473601
0.5172	Remote Similarity	NPC232611
0.5172	Remote Similarity	NPC63609
0.5161	Remote Similarity	NPC177818
0.5155	Remote Similarity	NPC144790
0.5155	Remote Similarity	NPC149400
0.5135	Remote Similarity	NPC475643
0.51	Remote Similarity	NPC242748
0.5085	Remote Similarity	NPC470862
0.5044	Remote Similarity	NPC471464
0.5044	Remote Similarity	NPC51172
0.5044	Remote Similarity	NPC49032
0.5041	Remote Similarity	NPC473505
0.504	Remote Similarity	NPC32707

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC319716 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7410
0.1-0.2	1618
0.2-0.3	111
0.3-0.4	5
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7614	Intermediate Similarity	NPD8171	Phase 2
0.6804	Remote Similarity	NPD8170	Phase 2
0.5268	Remote Similarity	NPD8450	Suspended
0.5225	Remote Similarity	NPD8449	Approved

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