NPASS Compound

Natural Product: NPC228083

Natural Product ID	NPC228083
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FMSINIOOEFEVRZ-JKKSTGMBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11040293
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 112118 0 0 0 0 0 0 0 0999 V2000 8.1245 2.3130 -2.9775 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4146 1.8834 -3.0315 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7056 0.5518 -3.1763 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6685 -0.3410 -3.2674 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3495 0.1100 -3.2128 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0362 1.4261 -3.0659 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7429 2.0573 -3.1139 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6425 1.6561 -2.5962 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4504 0.4696 -1.8133 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2494 0.1778 -1.4260 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3973 -0.3884 -1.4162 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3720 -1.5518 -0.6606 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8597 -1.4220 0.7495 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0377 -2.7324 1.4560 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1592 -2.6807 2.6871 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9084 -1.2243 3.0684 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0878 -0.5575 1.9571 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5411 -1.0673 0.7500 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8126 -0.9664 2.1674 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8038 -0.0925 2.2783 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3876 0.1722 3.7320 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2830 -1.0635 4.2562 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2397 -1.5519 3.2229 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4949 -2.1802 3.8025 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3171 -1.2480 4.3926 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5232 -0.6125 2.2619 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3623 -0.3987 1.4304 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7100 0.5322 0.4577 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0380 -0.0372 -0.7284 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2523 0.3243 -1.9374 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0614 0.6685 -3.1575 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2332 -0.2576 -3.2983 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7511 -1.4695 -4.1139 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8179 -2.3324 -4.3848 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7676 -0.7004 -2.1226 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4816 0.2493 -1.0592 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3622 -0.0882 -0.0115 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7074 0.1470 -0.1716 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 -0.9329 -0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7860 -1.9721 -1.0611 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7541 -0.7996 -0.9686 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4873 -1.8382 -1.5446 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8455 -1.6787 -1.7505 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4439 -0.5119 -1.3881 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7205 0.5105 -0.8213 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3465 0.3880 -0.5965 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6737 1.3683 -0.0578 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3461 1.2774 0.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6917 2.4285 0.7738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4556 2.4691 1.3268 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9495 3.6722 1.7988 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6513 4.8425 1.7345 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9018 4.8215 1.1817 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4191 3.6364 0.7070 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6453 6.0016 1.1023 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1273 6.0279 2.2107 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8261 -0.3482 -1.5963 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8293 -3.0040 -1.8948 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4116 2.0223 -3.1873 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5223 -0.7990 -2.3084 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6884 -2.0243 4.5504 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5179 1.2238 3.8178 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0252 -0.5345 3.4347 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8964 -3.1987 2.3425 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3659 -2.9829 1.8039 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0210 0.1042 -3.2308 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9526 3.3808 -2.8610 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2499 2.5648 -2.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8889 -1.3865 -3.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5692 -0.6415 -3.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6573 3.0346 -3.6775 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7113 2.2642 -2.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3949 -2.0214 -0.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7499 -2.2890 -1.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5124 -0.6219 1.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7028 -3.5489 0.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5322 -3.2399 3.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2725 -1.3022 4.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2574 0.5303 1.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2064 0.9307 1.9964 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2739 0.3531 4.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7864 -0.8684 5.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7200 -2.4087 2.6954 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9854 -2.7103 2.9347 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1679 -2.9870 4.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0775 -0.9852 3.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2950 -1.3792 0.9234 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9234 -1.1532 -0.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5078 1.1185 -1.7567 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3406 0.5261 -4.0293 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0349 0.1975 -3.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9733 -2.0217 -3.5791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3760 -1.1481 -5.1070 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8103 -2.6658 -5.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7324 1.1943 -1.5074 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4313 -2.4747 -2.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1635 1.4607 -0.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9077 1.5585 1.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9538 3.6965 2.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4163 3.6455 0.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6666 5.9059 1.1304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7752 6.7141 2.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0867 -0.1813 -2.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1841 -3.9029 -1.6322 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0259 2.2268 -3.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 -1.1547 -1.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0929 -1.8714 5.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1689 2.0744 3.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7176 -1.2041 3.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9037 -3.6170 1.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7035 -3.8462 1.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6732 0.3107 -2.4793 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 2 0 9 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 17 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 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 53 55 1 0 52 56 1 0 44 57 1 0 42 58 1 0 31 59 1 0 30 60 1 0 22 61 1 0 21 62 1 0 16 63 1 0 15 64 1 0 14 65 1 0 3 66 1 0 6 1 1 0 18 13 1 0 27 20 1 0 36 29 1 0 48 38 2 0 54 49 1 0 46 41 1 0 1 67 1 0 2 68 1 0 4 69 1 0 5 70 1 0 7 71 1 0 8 72 1 0 12 73 1 0 12 74 1 0 13 75 1 1 14 76 1 6 15 77 1 1 16 78 1 1 17 79 1 6 20 80 1 6 21 81 1 1 22 82 1 1 23 83 1 6 24 84 1 0 24 85 1 0 25 86 1 0 27 87 1 6 29 88 1 1 30 89 1 1 31 90 1 6 32 91 1 6 33 92 1 0 33 93 1 0 34 94 1 0 36 95 1 6 43 96 1 0 45 97 1 0 50 98 1 0 51 99 1 0 54100 1 0 55101 1 0 56102 1 0 57103 1 0 58104 1 0 59105 1 0 60106 1 0 61107 1 0 62108 1 0 63109 1 0 64110 1 0 65111 1 0 66112 1 0 M END

Standard InCHIKey	FMSINIOOEFEVRZ-JKKSTGMBSA-N
Standard InCHI	InChI=1S/C42H46O24/c43-12-23-29(52)34(57)39(41(61-23)64-37-31(54)27-21(49)10-18(46)11-22(27)60-36(37)16-4-7-19(47)20(48)9-16)66-42-38(33(56)28(51)24(13-44)62-42)65-40-35(58)32(55)30(53)25(63-40)14-59-26(50)8-3-15-1-5-17(45)6-2-15/h1-11,23-25,28-30,32-35,38-49,51-53,55-58H,12-14H2/b8-3-/t23-,24-,25-,28-,29-,30-,32+,33+,34+,35-,38-,39-,40+,41+,42+/m1/s1
SMILES	c1cc(ccc1/C=CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	934.24	Volume:	851.784 ? Van der Waals volume.
Dense:	1.097	LogP:	-0.207 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.236 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.045 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	44.0
TPSA:	395.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	14.0	Rings:	7.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.036	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.724	Fsp³:	0.429
MCE-18:	171.5 ? 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:	0.692	Fluc inhibitor:	0.533 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.697 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.39	Promiscuous compounds:	0.591

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.746	MDCK Permeability:	-5.004
Pgp-inhibitor:	0.0	Pgp-substrate:	0.02
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):	1.0
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	84.365%	Volume Distribution (VD):	-0.065
Fu:	14.564% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.016
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.033 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.815

Half-life (T1/2):

5.449

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.112
Human Hepatotoxicity (H-HT):	0.591	Drug-induced Liver Injury (DILI):	0.844
AMES Toxicity:	0.868	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.011	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.11	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.992
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.476
Genotoxicity:	0.883	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.908
BCF:	0.509 ? 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:	3.263 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.862 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.131 ? 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
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15286289]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[20947202]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253552]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Wax	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11043	Pisum sativum	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 NPC228083 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	18521
0.1-0.2	26527
0.2-0.3	3827
0.3-0.4	602
0.4-0.5	175
0.5-0.6	137
0.6-0.7	51
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8532	High Similarity	NPC21359
0.8532	High Similarity	NPC460984
0.8108	Intermediate Similarity	NPC25946
0.7453	Intermediate Similarity	NPC223426
0.7193	Intermediate Similarity	NPC162394
0.719	Intermediate Similarity	NPC249560
0.7107	Intermediate Similarity	NPC487502
0.6972	Remote Similarity	NPC218161
0.6961	Remote Similarity	NPC254855
0.6961	Remote Similarity	NPC94610
0.6944	Remote Similarity	NPC85751
0.6944	Remote Similarity	NPC19240
0.6909	Remote Similarity	NPC81042
0.686	Remote Similarity	NPC473554
0.6752	Remote Similarity	NPC488740
0.6752	Remote Similarity	NPC488736
0.6752	Remote Similarity	NPC488733
0.6698	Remote Similarity	NPC155877
0.6696	Remote Similarity	NPC470718
0.6667	Remote Similarity	NPC470712
0.6639	Remote Similarity	NPC488737
0.6636	Remote Similarity	NPC255157
0.6636	Remote Similarity	NPC259896
0.6607	Remote Similarity	NPC214621
0.6607	Remote Similarity	NPC34267
0.6579	Remote Similarity	NPC477895
0.6538	Remote Similarity	NPC170052
0.6538	Remote Similarity	NPC135846
0.6522	Remote Similarity	NPC217520
0.6455	Remote Similarity	NPC122467
0.6434	Remote Similarity	NPC487501
0.6372	Remote Similarity	NPC602448
0.6349	Remote Similarity	NPC30011
0.6303	Remote Similarity	NPC488734
0.6303	Remote Similarity	NPC488735
0.6303	Remote Similarity	NPC488739
0.6303	Remote Similarity	NPC488732
0.6303	Remote Similarity	NPC488738
0.6296	Remote Similarity	NPC163242
0.6296	Remote Similarity	NPC272068
0.6283	Remote Similarity	NPC292929
0.6241	Remote Similarity	NPC33083
0.6239	Remote Similarity	NPC304741
0.6239	Remote Similarity	NPC156869
0.6231	Remote Similarity	NPC487500
0.623	Remote Similarity	NPC241781
0.622	Remote Similarity	NPC72554
0.619	Remote Similarity	NPC275977
0.6148	Remote Similarity	NPC480444
0.6134	Remote Similarity	NPC139571
0.6071	Remote Similarity	NPC12013
0.6071	Remote Similarity	NPC11432
0.6071	Remote Similarity	NPC477613
0.6066	Remote Similarity	NPC156785
0.6053	Remote Similarity	NPC89127
0.6031	Remote Similarity	NPC97817
0.6019	Remote Similarity	NPC95866
0.6	Remote Similarity	NPC470405
0.5984	Remote Similarity	NPC470713
0.5982	Remote Similarity	NPC253521
0.5982	Remote Similarity	NPC113836
0.5966	Remote Similarity	NPC303694
0.5938	Remote Similarity	NPC231787
0.5913	Remote Similarity	NPC471669
0.5913	Remote Similarity	NPC220173
0.5913	Remote Similarity	NPC477629
0.5897	Remote Similarity	NPC96605
0.5897	Remote Similarity	NPC280642
0.5872	Remote Similarity	NPC116864
0.5872	Remote Similarity	NPC244776
0.5862	Remote Similarity	NPC36138
0.5854	Remote Similarity	NPC480445
0.5833	Remote Similarity	NPC164704
0.5826	Remote Similarity	NPC221288
0.5826	Remote Similarity	NPC194836
0.5826	Remote Similarity	NPC91493
0.5826	Remote Similarity	NPC605081
0.5776	Remote Similarity	NPC76831
0.575	Remote Similarity	NPC219043
0.575	Remote Similarity	NPC292019
0.575	Remote Similarity	NPC202908
0.5741	Remote Similarity	NPC224530
0.5726	Remote Similarity	NPC260504
0.5726	Remote Similarity	NPC89809
0.5726	Remote Similarity	NPC221342
0.5726	Remote Similarity	NPC476470
0.5714	Remote Similarity	NPC89052
0.5714	Remote Similarity	NPC67326
0.5702	Remote Similarity	NPC61904
0.5702	Remote Similarity	NPC470125
0.5702	Remote Similarity	NPC470715
0.5664	Remote Similarity	NPC203259
0.5664	Remote Similarity	NPC33054
0.5664	Remote Similarity	NPC176740
0.5664	Remote Similarity	NPC471725
0.5664	Remote Similarity	NPC134532
0.5664	Remote Similarity	NPC602582
0.5652	Remote Similarity	NPC477628
0.5636	Remote Similarity	NPC476215
0.5635	Remote Similarity	NPC488078
0.563	Remote Similarity	NPC478277
0.563	Remote Similarity	NPC483765
0.563	Remote Similarity	NPC478276
0.563	Remote Similarity	NPC478275
0.563	Remote Similarity	NPC92815
0.5625	Remote Similarity	NPC480472
0.562	Remote Similarity	NPC48984
0.5615	Remote Similarity	NPC487499
0.5556	Remote Similarity	NPC205824
0.5547	Remote Similarity	NPC192539
0.5546	Remote Similarity	NPC483767
0.5546	Remote Similarity	NPC483769
0.5546	Remote Similarity	NPC483768
0.5546	Remote Similarity	NPC483766
0.5538	Remote Similarity	NPC480470
0.552	Remote Similarity	NPC474093
0.552	Remote Similarity	NPC104910
0.5514	Remote Similarity	NPC145038
0.5514	Remote Similarity	NPC56077
0.5514	Remote Similarity	NPC281131
0.5514	Remote Similarity	NPC253662
0.5514	Remote Similarity	NPC179950
0.5514	Remote Similarity	NPC88789
0.5514	Remote Similarity	NPC491374
0.5487	Remote Similarity	NPC29958
0.547	Remote Similarity	NPC104883
0.547	Remote Similarity	NPC488679
0.5447	Remote Similarity	NPC480441
0.5439	Remote Similarity	NPC471748
0.5424	Remote Similarity	NPC101399
0.5424	Remote Similarity	NPC97119
0.5424	Remote Similarity	NPC217822
0.5424	Remote Similarity	NPC11847
0.5424	Remote Similarity	NPC198938
0.5424	Remote Similarity	NPC472991
0.541	Remote Similarity	NPC470416
0.541	Remote Similarity	NPC488075
0.541	Remote Similarity	NPC189564
0.5366	Remote Similarity	NPC173837
0.5351	Remote Similarity	NPC471079
0.5345	Remote Similarity	NPC129264
0.5345	Remote Similarity	NPC470444
0.5339	Remote Similarity	NPC37668
0.5312	Remote Similarity	NPC474522
0.5312	Remote Similarity	NPC470717
0.5304	Remote Similarity	NPC173582
0.5304	Remote Similarity	NPC265885
0.5304	Remote Similarity	NPC181465
0.5304	Remote Similarity	NPC215710
0.5304	Remote Similarity	NPC473438
0.5304	Remote Similarity	NPC253788
0.5299	Remote Similarity	NPC488073
0.5299	Remote Similarity	NPC240306
0.5271	Remote Similarity	NPC470720
0.5268	Remote Similarity	NPC136761
0.5259	Remote Similarity	NPC223860
0.5254	Remote Similarity	NPC480471
0.5254	Remote Similarity	NPC488076
0.5234	Remote Similarity	NPC67037
0.5234	Remote Similarity	NPC255615
0.5225	Remote Similarity	NPC175107
0.5214	Remote Similarity	NPC35167
0.521	Remote Similarity	NPC473327
0.5203	Remote Similarity	NPC203145
0.52	Remote Similarity	NPC25523
0.5169	Remote Similarity	NPC153755
0.5167	Remote Similarity	NPC603079
0.5143	Remote Similarity	NPC475179
0.5138	Remote Similarity	NPC77672
0.5138	Remote Similarity	NPC133671
0.5138	Remote Similarity	NPC135391
0.5138	Remote Similarity	NPC78263
0.5138	Remote Similarity	NPC250069
0.513	Remote Similarity	NPC473682
0.5128	Remote Similarity	NPC605592
0.5124	Remote Similarity	NPC80068
0.5124	Remote Similarity	NPC473071
0.5089	Remote Similarity	NPC60735
0.5089	Remote Similarity	NPC26230
0.5086	Remote Similarity	NPC139320
0.5085	Remote Similarity	NPC144097
0.5083	Remote Similarity	NPC32641
0.5083	Remote Similarity	NPC256188
0.5083	Remote Similarity	NPC270448
0.5083	Remote Similarity	NPC35119
0.5077	Remote Similarity	NPC470719
0.5044	Remote Similarity	NPC120099
0.5043	Remote Similarity	NPC39834
0.5042	Remote Similarity	NPC472992
0.5042	Remote Similarity	NPC154741
0.5041	Remote Similarity	NPC142142
0.5041	Remote Similarity	NPC270675
0.5041	Remote Similarity	NPC195685
0.5039	Remote Similarity	NPC295625
0.5038	Remote Similarity	NPC488079

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC228083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5177
0.1-0.2	3923
0.2-0.3	40
0.3-0.4	8
0.4-0.5	1
0.5-0.6	1
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
0.5664	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