NPASS Compound

Natural Product: NPC309223

Natural Product ID	NPC309223
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CKBVDWQFFMQIGU-BLWFDAFZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3357157
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 215226 0 0 0 0 0 0 0 0999 V2000 6.1386 3.7404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 1.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 4.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 4.5883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 6.0655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8195 7.3646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7186 7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1281 6.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 5.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1386 3.7404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6281 6.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4686 8.3287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7186 9.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1281 10.1408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 11.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 12.5822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 12.0692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 10.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8195 9.2929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3300 12.0692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 13.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5691 12.4040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9786 12.9171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2391 14.3943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0900 15.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3195 14.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8195 14.8454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3400 16.6575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9891 15.6933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 13.8812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 -0.5130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7981 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2981 1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 -0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5586 -2.1469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 -3.4460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2181 -3.9590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4786 -5.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2286 -6.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3296 -6.4004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9200 -5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6595 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 -3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4200 -5.8874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5796 -7.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -1.6339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 -9.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0105 -10.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -10.5705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1386 -11.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -12.4988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -13.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -15.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7291 -16.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3195 -17.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0695 -18.7425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3195 -20.0416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8195 -20.0416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0695 -18.7425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8195 -17.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0800 -15.9663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0796 -17.7784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4100 -20.5546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6595 -14.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -13.5249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5481 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -10.5705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2181 -13.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -15.4533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 1.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 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0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 2 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 64 68 1 6 63 69 1 1 63 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 1 73 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 78 80 1 0 77 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 88 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 92 93 1 0 91 94 1 0 90 95 1 0 84 96 1 0 96 97 1 0 97 98 1 0 98 99 1 0 97100 1 0 96101 1 0 56102 1 0 56103 1 0 36 2 1 0 46 40 1 0 66 53 1 0 78 72 1 0 98 82 1 0 11 5 1 0 20 15 1 0 28 23 1 0 58 53 1 0 64 59 1 0 92 87 1 0 73 62 1 0 1104 1 0 2105 1 6 3106 1 1 5107 1 1 7108 1 6 8109 1 0 8110 1 0 8111 1 0 9112 1 1 10113 1 6 11114 1 6 12115 1 0 13116 1 0 15117 1 6 17118 1 0 17119 1 0 18120 1 1 19121 1 6 20122 1 1 21123 1 0 23124 1 1 25125 1 0 25126 1 0 26127 1 6 27128 1 1 28129 1 6 29130 1 0 30131 1 0 31132 1 0 32133 1 0 33134 1 6 35135 1 6 36136 1 1 37137 1 0 38138 1 0 38139 1 0 40140 1 1 42141 1 6 43142 1 0 43143 1 0 43144 1 0 44145 1 1 45146 1 6 46147 1 6 47148 1 0 48149 1 0 49150 1 0 54151 1 0 54152 1 0 55153 1 0 55154 1 0 57155 1 0 57156 1 0 58157 1 1 60158 1 0 61159 1 0 61160 1 0 62161 1 6 65162 1 0 65163 1 0 66164 1 1 67165 1 0 68166 1 0 68167 1 0 68168 1 0 69169 1 0 69170 1 0 69171 1 0 70172 1 0 70173 1 0 71174 1 0 71175 1 0 72176 1 6 74177 1 0 74178 1 0 74179 1 0 75180 1 0 75181 1 0 76182 1 0 76183 1 0 77184 1 6 79185 1 0 79186 1 0 79187 1 0 80188 1 0 80189 1 0 80190 1 0 82191 1 1 84192 1 1 85193 1 0 85194 1 0 87195 1 6 89196 1 0 89197 1 0 90198 1 6 91199 1 6 92200 1 1 93201 1 0 94202 1 0 95203 1 0 96204 1 6 97205 1 1 98206 1 6 99207 1 0 100208 1 0 101209 1 0 102210 1 0 102211 1 0 102212 1 0 103213 1 0 103214 1 0 103215 1 0 M END

Standard InCHIKey	CKBVDWQFFMQIGU-BLWFDAFZSA-N
Standard InCHI	InChI=1S/C69H112O34/c1-25-38(74)43(79)49(85)57(95-25)94-24-33-42(78)45(81)55(102-60-51(87)46(82)53(26(2)96-60)100-59-52(88)54(31(72)22-92-59)101-58-48(84)40(76)30(71)21-91-58)62(98-33)103-63(89)69-17-16-64(3,4)18-28(69)27-10-11-35-66(7)14-13-37(65(5,6)34(66)12-15-67(35,8)68(27,9)19-36(69)73)99-61-50(86)44(80)41(77)32(97-61)23-93-56-47(83)39(75)29(70)20-90-56/h10,25-26,28-62,70-88H,11-24H2,1-9H3/t25-,26-,28-,29-,30+,31+,32+,33+,34-,35+,36+,37-,38-,39-,40-,41+,42+,43+,44-,45-,46-,47+,48+,49+,50+,51+,52+,53-,54-,55+,56-,57+,58-,59-,60-,61-,62-,66-,67+,68+,69+/m0/s1
SMILES	O[C@@H]1[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O)[C@@H](O[C@@H]([C@H]1O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)OC(=O)[C@@]12CCC(C[C@H]2C2=CC[C@H]3[C@@]([C@@]2(C[C@H]1O)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O[C@@H]1O[C@H](CO[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1484.7	Volume:	1392.897 ? Van der Waals volume.
Dense:	1.066	LogP:	0.883 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.502 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.622 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	69.0
TPSA:	530.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	34.0
H-Bond Donor:	19.0	Rings:	12.0
Heavy Atoms:	34.0

MedChem Properties

QED Drug-Likeness Score:	0.039	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.666	Fsp³:	0.957
MCE-18:	261.778 ? 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:	0.68	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.411	Promiscuous compounds:	0.066

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.013	MDCK Permeability:	-5.017
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	0.93
20% Bioavailability (F20%):	0.266	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):	44.475%	Volume Distribution (VD):	-0.295
Fu:	33.625% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

-1.102

Half-life (T1/2):

4.586

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.546	Drug-induced Liver Injury (DILI):	0.887
AMES Toxicity:	0.976	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.25	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.006	RPMI-8226 Immunitoxicity:	0.504
A549 Cytotoxicity:	0.923	Hek293 Cytotoxicity:	0.405
BCF:	0.973 ? 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:	3.406 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.836 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.765 ? 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
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	anomalous fruits	n.a.	n.a.	PMID[25442304]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20608	Gleditsia sinensis	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

Activity Type	# Activity
Activity	2

Activity Type	# Activity
Cell line	2

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
NPT380	Cell line	U-251	Homo sapiens	Activity	=	72.35	%	PMID[25442304]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	63.93	%	PMID[25442304]

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 NPC309223 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	24427
0.1-0.2	21842
0.2-0.3	2491
0.3-0.4	624
0.4-0.5	266
0.5-0.6	131
0.6-0.7	46
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC102505
0.9478	High Similarity	NPC488514
0.8947	High Similarity	NPC13998
0.8197	Intermediate Similarity	NPC224381
0.7983	Intermediate Similarity	NPC85154
0.7917	Intermediate Similarity	NPC473386
0.775	Intermediate Similarity	NPC471577
0.7656	Intermediate Similarity	NPC8524
0.7597	Intermediate Similarity	NPC33012
0.75	Intermediate Similarity	NPC471580
0.7394	Intermediate Similarity	NPC472270
0.7394	Intermediate Similarity	NPC112492
0.736	Intermediate Similarity	NPC475514
0.728	Intermediate Similarity	NPC286457
0.7266	Intermediate Similarity	NPC70809
0.7227	Intermediate Similarity	NPC104137
0.7227	Intermediate Similarity	NPC26626
0.7222	Intermediate Similarity	NPC470876
0.7143	Intermediate Similarity	NPC480421
0.7131	Intermediate Similarity	NPC123522
0.7077	Intermediate Similarity	NPC220160
0.704	Intermediate Similarity	NPC488560
0.6957	Remote Similarity	NPC297950
0.6944	Remote Similarity	NPC23020
0.6906	Remote Similarity	NPC472268
0.6866	Remote Similarity	NPC480422
0.678	Remote Similarity	NPC488526
0.6744	Remote Similarity	NPC473452
0.6693	Remote Similarity	NPC480423
0.6639	Remote Similarity	NPC164389
0.6639	Remote Similarity	NPC481079
0.6562	Remote Similarity	NPC475160
0.6562	Remote Similarity	NPC473714
0.6538	Remote Similarity	NPC237191
0.6463	Remote Similarity	NPC485563
0.6446	Remote Similarity	NPC105800
0.6434	Remote Similarity	NPC329893
0.6418	Remote Similarity	NPC144644
0.6418	Remote Similarity	NPC170407
0.6356	Remote Similarity	NPC480420
0.6343	Remote Similarity	NPC236638
0.6343	Remote Similarity	NPC294453
0.632	Remote Similarity	NPC295823
0.632	Remote Similarity	NPC174720
0.632	Remote Similarity	NPC475467
0.6296	Remote Similarity	NPC37860
0.6288	Remote Similarity	NPC476068
0.6232	Remote Similarity	NPC68767
0.6225	Remote Similarity	NPC472269
0.6176	Remote Similarity	NPC302543
0.6159	Remote Similarity	NPC250247
0.6154	Remote Similarity	NPC1046
0.6133	Remote Similarity	NPC311178
0.6133	Remote Similarity	NPC478559
0.6133	Remote Similarity	NPC478560
0.6115	Remote Similarity	NPC293031
0.6098	Remote Similarity	NPC232237
0.6094	Remote Similarity	NPC815
0.609	Remote Similarity	NPC481080
0.6087	Remote Similarity	NPC482010
0.6083	Remote Similarity	NPC173583
0.6045	Remote Similarity	NPC21691
0.6042	Remote Similarity	NPC489208
0.6027	Remote Similarity	NPC484831
0.6016	Remote Similarity	NPC207738
0.6014	Remote Similarity	NPC484829
0.6	Remote Similarity	NPC60557
0.6	Remote Similarity	NPC67857
0.5987	Remote Similarity	NPC222951
0.5985	Remote Similarity	NPC305981
0.5985	Remote Similarity	NPC481081
0.5973	Remote Similarity	NPC233223
0.5973	Remote Similarity	NPC183816
0.5973	Remote Similarity	NPC43589
0.597	Remote Similarity	NPC4749
0.5963	Remote Similarity	NPC488513
0.5942	Remote Similarity	NPC261506
0.5942	Remote Similarity	NPC4328
0.5933	Remote Similarity	NPC475584
0.5933	Remote Similarity	NPC475152
0.5926	Remote Similarity	NPC57484
0.5918	Remote Similarity	NPC484830
0.5906	Remote Similarity	NPC329878
0.587	Remote Similarity	NPC202828
0.587	Remote Similarity	NPC119592
0.5865	Remote Similarity	NPC475209
0.5865	Remote Similarity	NPC135904
0.5865	Remote Similarity	NPC123199
0.5846	Remote Similarity	NPC11242
0.5845	Remote Similarity	NPC489209
0.5839	Remote Similarity	NPC41061
0.5839	Remote Similarity	NPC227551
0.5828	Remote Similarity	NPC300655
0.5828	Remote Similarity	NPC196874
0.5823	Remote Similarity	NPC324933
0.5822	Remote Similarity	NPC475177
0.5814	Remote Similarity	NPC241909
0.58	Remote Similarity	NPC475394
0.5797	Remote Similarity	NPC43550
0.5759	Remote Similarity	NPC322904
0.5746	Remote Similarity	NPC480419
0.5745	Remote Similarity	NPC142151
0.5742	Remote Similarity	NPC488619
0.5734	Remote Similarity	NPC153673
0.5726	Remote Similarity	NPC76497
0.5714	Remote Similarity	NPC33068
0.5714	Remote Similarity	NPC79643
0.5704	Remote Similarity	NPC283417
0.5704	Remote Similarity	NPC200049
0.5687	Remote Similarity	NPC319719
0.5682	Remote Similarity	NPC172365
0.5664	Remote Similarity	NPC480417
0.5652	Remote Similarity	NPC265699
0.5652	Remote Similarity	NPC110633
0.5641	Remote Similarity	NPC475444
0.5641	Remote Similarity	NPC473679
0.5634	Remote Similarity	NPC267694
0.5625	Remote Similarity	NPC110385
0.5625	Remote Similarity	NPC51099
0.5621	Remote Similarity	NPC13989
0.5616	Remote Similarity	NPC275225
0.5591	Remote Similarity	NPC173859
0.5577	Remote Similarity	NPC488618
0.5564	Remote Similarity	NPC185466
0.5556	Remote Similarity	NPC470911
0.5532	Remote Similarity	NPC136768
0.5522	Remote Similarity	NPC76972
0.5522	Remote Similarity	NPC469782
0.5522	Remote Similarity	NPC204414
0.55	Remote Similarity	NPC100612
0.5493	Remote Similarity	NPC298034
0.5493	Remote Similarity	NPC71065
0.5493	Remote Similarity	NPC482012
0.5484	Remote Similarity	NPC475516
0.5469	Remote Similarity	NPC305267
0.5462	Remote Similarity	NPC64715
0.5455	Remote Similarity	NPC69811
0.5436	Remote Similarity	NPC475368
0.5429	Remote Similarity	NPC480418
0.5426	Remote Similarity	NPC63159
0.542	Remote Similarity	NPC37134
0.5414	Remote Similarity	NPC481078
0.5391	Remote Similarity	NPC117714
0.539	Remote Similarity	NPC45606
0.539	Remote Similarity	NPC258617
0.5375	Remote Similarity	NPC113620
0.5373	Remote Similarity	NPC210729
0.5373	Remote Similarity	NPC82931
0.5368	Remote Similarity	NPC192600
0.5361	Remote Similarity	NPC475527
0.5357	Remote Similarity	NPC476113
0.5355	Remote Similarity	NPC475892
0.5352	Remote Similarity	NPC293330
0.5352	Remote Similarity	NPC65105
0.5349	Remote Similarity	NPC148603
0.5344	Remote Similarity	NPC484832
0.5333	Remote Similarity	NPC488204
0.5328	Remote Similarity	NPC165204
0.5323	Remote Similarity	NPC48499
0.5298	Remote Similarity	NPC174336
0.5294	Remote Similarity	NPC475287
0.529	Remote Similarity	NPC155410
0.5276	Remote Similarity	NPC470512
0.5276	Remote Similarity	NPC488620
0.5256	Remote Similarity	NPC220838
0.5252	Remote Similarity	NPC475140
0.5245	Remote Similarity	NPC161717
0.5234	Remote Similarity	NPC469946
0.521	Remote Similarity	NPC488201
0.5205	Remote Similarity	NPC482011
0.52	Remote Similarity	NPC475208
0.5194	Remote Similarity	NPC112352
0.5182	Remote Similarity	NPC610204
0.5181	Remote Similarity	NPC481324
0.5174	Remote Similarity	NPC187497
0.5172	Remote Similarity	NPC476991
0.5156	Remote Similarity	NPC295371
0.5156	Remote Similarity	NPC488516
0.5154	Remote Similarity	NPC104071
0.5154	Remote Similarity	NPC30289
0.5152	Remote Similarity	NPC470513
0.5152	Remote Similarity	NPC488517
0.5147	Remote Similarity	NPC470915
0.5143	Remote Similarity	NPC100639
0.5135	Remote Similarity	NPC478825
0.5123	Remote Similarity	NPC469776
0.5116	Remote Similarity	NPC263756
0.5115	Remote Similarity	NPC102439
0.5113	Remote Similarity	NPC488515
0.5106	Remote Similarity	NPC25663
0.5102	Remote Similarity	NPC478823
0.5091	Remote Similarity	NPC469778
0.5076	Remote Similarity	NPC148417
0.5074	Remote Similarity	NPC31838
0.5072	Remote Similarity	NPC473824
0.5071	Remote Similarity	NPC257211
0.5071	Remote Similarity	NPC603137
0.5038	Remote Similarity	NPC470514
0.5038	Remote Similarity	NPC123796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC309223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7822
0.1-0.2	1285
0.2-0.3	41
0.3-0.4	2
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