NPASS Compound

Natural Product: NPC477464

Natural Product ID	NPC477464
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bR)-9-[[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-8,10,11-trihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
IUPAC Name	[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bR)-9-[[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-8,10,11-trihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44566729
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 3D 217228 0 0 0 0 0 0 0 0999 V2000 15.6375 -1.4883 2.8021 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8568 -1.1720 1.3505 C 0 0 1 0 0 0 0 0 0 0 0 0 16.3269 -2.3654 0.5519 C 0 0 1 0 0 0 0 0 0 0 0 0 15.7996 -2.1450 -0.8712 C 0 0 2 0 0 0 0 0 0 0 0 0 14.2699 -2.2277 -0.8855 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7976 -1.7607 0.4613 C 0 0 1 0 0 0 0 0 0 0 0 0 14.6880 -0.6948 0.8039 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5603 -1.1743 0.4115 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6395 -1.6347 1.3449 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4772 -2.2407 0.6302 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2591 -1.7406 1.0901 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1956 -0.3948 0.7676 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1496 0.3613 1.6272 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2024 -0.5083 2.2677 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7940 -1.0335 3.4867 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7686 1.4120 0.9568 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5368 2.6661 1.4004 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8593 3.2620 1.8922 C 0 0 1 0 0 0 0 0 0 0 0 0 12.5856 3.9368 0.7456 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0864 3.4218 -0.5687 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6265 3.6940 -0.6967 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9770 3.5342 0.4884 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8102 3.9365 -1.6477 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9568 3.7504 0.9147 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6530 4.1341 2.9662 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8751 -0.0154 1.1091 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 0.4208 0.0196 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6797 1.8278 0.2821 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5563 1.8808 1.2962 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9897 0.6196 1.4919 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7120 -0.0173 0.3149 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0025 -0.5250 -0.3017 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2584 -1.8139 0.1510 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9899 0.7386 -0.6086 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8030 0.1242 -0.9832 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8892 -0.3523 -2.4420 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0417 0.8479 -3.3466 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0709 1.8967 -2.8014 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.2711 -2.0517 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5782 0.9640 -0.7651 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6059 0.1781 -0.1150 O 0 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0 -15.4208 2.9757 2.8704 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.9446 2.1659 0.5791 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9698 1.4887 -4.0655 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0625 -0.2436 -4.7293 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3672 3.0351 -1.7053 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9298 2.4788 0.8449 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9380 2.6311 1.1395 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9842 -1.1321 0.5753 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2971 -1.8666 -0.5166 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4530 -2.9434 0.1129 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3330 -2.5227 1.2997 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3159 -1.5891 2.2485 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4954 -3.4615 -0.9451 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3244 -4.1415 0.5216 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4994 -0.8801 1.9066 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7036 0.4440 -4.6265 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7029 -1.0336 -2.7058 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0601 2.3650 2.6373 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3434 2.5064 -0.8891 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3823 -3.7517 0.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5091 -4.4166 0.4962 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9561 -3.5514 -1.0898 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3668 -3.1563 -1.6447 O 0 0 0 0 0 0 0 0 0 0 0 0 17.7191 -2.2932 0.4641 O 0 0 0 0 0 0 0 0 0 0 0 0 16.1962 -2.3602 3.1371 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5490 -1.6900 2.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8504 -0.5785 3.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6228 -0.3759 1.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0035 -3.3276 0.9761 H 0 0 0 0 0 0 0 0 0 0 0 0 16.1216 -1.1436 -1.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8649 -1.5690 -1.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9209 -2.5767 1.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1380 -2.4183 1.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5131 -2.1058 -0.4624 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3667 -0.2629 -0.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5686 0.8202 2.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0908 0.1144 2.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1012 -0.4617 3.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8586 2.6908 2.2959 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5091 2.4449 2.2581 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3665 5.0054 0.7997 H 0 0 0 0 0 0 0 0 0 0 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37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 44 42 1 6 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 6 60 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 68 70 1 0 70 71 1 0 67 72 1 0 66 73 1 0 65 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 80 81 1 0 77 82 1 1 76 83 1 0 59 84 1 0 58 85 1 0 56 86 1 6 54 87 1 0 52 88 1 6 48 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 92 93 1 0 91 94 1 0 91 95 1 0 47 96 1 1 37 97 1 0 36 98 1 0 29 99 1 0 28100 1 0 10101 1 0 101102 1 0 5103 1 0 4104 1 0 3105 1 0 7 2 1 0 60 55 1 0 69 64 1 0 79 75 1 0 14 9 1 0 22 17 1 0 32 27 1 0 40 35 1 0 89 44 1 0 93 44 1 0 52 47 1 0 56 51 1 0 1106 1 0 1107 1 0 1108 1 0 2109 1 1 3110 1 1 4111 1 6 5112 1 6 6113 1 1 9114 1 1 10115 1 6 12116 1 6 13117 1 1 14118 1 1 15119 1 0 17120 1 1 18121 1 1 19122 1 6 20123 1 1 21124 1 0 21125 1 0 23126 1 0 24127 1 0 25128 1 0 27129 1 6 28130 1 1 29131 1 6 31132 1 1 32133 1 6 33134 1 0 35135 1 1 36136 1 1 37137 1 6 38138 1 0 38139 1 0 40140 1 1 45141 1 0 45142 1 0 46143 1 0 46144 1 0 49145 1 0 50146 1 0 50147 1 0 51148 1 1 53149 1 0 53150 1 0 54151 1 1 55152 1 1 57153 1 0 57154 1 0 58155 1 1 59156 1 1 61157 1 0 61158 1 0 61159 1 0 62160 1 0 62161 1 0 64162 1 1 65163 1 6 66164 1 1 67165 1 6 68166 1 1 70167 1 0 70168 1 0 71169 1 0 72170 1 0 73171 1 0 75172 1 6 76173 1 1 78174 1 0 78175 1 0 80176 1 0 80177 1 0 81178 1 0 82179 1 0 83180 1 0 84181 1 0 85182 1 0 86183 1 0 86184 1 0 86185 1 0 87186 1 0 88187 1 0 88188 1 0 88189 1 0 89190 1 1 90191 1 0 90192 1 0 92193 1 0 92194 1 0 93195 1 0 93196 1 0 94197 1 0 94198 1 0 94199 1 0 95200 1 0 95201 1 0 95202 1 0 96203 1 0 96204 1 0 96205 1 0 97206 1 0 98207 1 0 99208 1 0 99209 1 0 99210 1 0 100211 1 0 101212 1 0 101213 1 0 102214 1 0 103215 1 0 104216 1 0 105217 1 0 M END

Standard InCHIKey	VPOXKIWAMFSFCI-SMFVNLDXSA-N
Standard InCHI	InChI=1S/C69H112O36/c1-25-36(77)41(82)44(85)56(96-25)100-47-34(19-71)99-60(51(45(47)86)102-55-43(84)38(79)31(75)20-92-55)101-48-37(78)26(2)97-57(46(48)87)103-49-39(80)32(76)21-93-58(49)105-62(90)68-13-11-63(3,4)15-28(68)27-9-10-35-64(5)16-30(74)53(88)65(6,52(64)29(73)17-67(35,8)66(27,7)12-14-68)23-94-59-50(42(83)40(81)33(18-70)98-59)104-61-54(89)69(91,22-72)24-95-61/h9,25-26,28-61,70-89,91H,10-24H2,1-8H3/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-,64+,65-,66+,67+,68-,69+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O[C@@H]4[C@H]([C@@H](O[C@H]([C@@H]4O)O[C@@H]5[C@H]([C@H](CO[C@H]5OC(=O)[C@@]67CC[C@@]8(C(=CC[C@H]9[C@]8(C[C@H]([C@@H]1[C@@]9(C[C@@H]([C@@H]([C@@]1(C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]1[C@@H]([C@](CO1)(CO)O)O)O)O)C)O)C)[C@H]6CC(CC7)(C)C)C)O)O)C)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1516.69	Volume:	1410.477 ? Van der Waals volume.
Dense:	1.075	LogP:	0.139 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.892 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.534 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	68.0
TPSA:	571.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	36.0
H-Bond Donor:	21.0	Rings:	12.0
Heavy Atoms:	36.0

MedChem Properties

QED Drug-Likeness Score:	0.045	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.96	Fsp³:	0.957
MCE-18:	266.0 ? 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:	0.663	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.4	Promiscuous compounds:	0.364

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.468	MDCK Permeability:	-4.713
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.007	MRP1:	0.111
Plasma Protein Binding (PPB):	63.053%	Volume Distribution (VD):	-0.336
Fu:	19.201% ? 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:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.341 ? 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):

-1.831

Half-life (T1/2):

5.463

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.793	Drug-induced Liver Injury (DILI):	0.955
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.839	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.634	RPMI-8226 Immunitoxicity:	0.769
A549 Cytotoxicity:	0.994	Hek293 Cytotoxicity:	0.626
BCF:	0.732 ? 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:	3.279 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.81 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.791 ? 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
NPO31375	Madhuca indica	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104500]
NPO31375	Madhuca indica	Species	Sapotaceae	Eukaryota	n.a.	bark	n.a.	PMID[15104500]
NPO31375	Madhuca indica	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
IC50	1
Inhibition	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	144	ug/ml	PMID[15104500]
NPT2	Others	Unspecified	n.a.	Inhibition	=	16	%	PMID[15104500]

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 NPC477464 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	27319
0.1-0.2	19707
0.2-0.3	2089
0.3-0.4	501
0.4-0.5	182
0.5-0.6	57
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.808	Intermediate Similarity	NPC477463
0.6324	Remote Similarity	NPC57484
0.5956	Remote Similarity	NPC475899
0.5821	Remote Similarity	NPC481078
0.5804	Remote Similarity	NPC202828
0.5804	Remote Similarity	NPC119592
0.5804	Remote Similarity	NPC236638
0.5804	Remote Similarity	NPC294453
0.5704	Remote Similarity	NPC473645
0.5694	Remote Similarity	NPC305981
0.5655	Remote Similarity	NPC261506
0.5655	Remote Similarity	NPC298034
0.5655	Remote Similarity	NPC71065
0.5655	Remote Similarity	NPC4328
0.5646	Remote Similarity	NPC250247
0.5625	Remote Similarity	NPC293330
0.558	Remote Similarity	NPC475287
0.5571	Remote Similarity	NPC123199
0.5556	Remote Similarity	NPC41061
0.5556	Remote Similarity	NPC227551
0.5533	Remote Similarity	NPC480422
0.5486	Remote Similarity	NPC480418
0.5448	Remote Similarity	NPC470876
0.5448	Remote Similarity	NPC475504
0.5429	Remote Similarity	NPC79643
0.54	Remote Similarity	NPC480417
0.5357	Remote Similarity	NPC300419
0.5306	Remote Similarity	NPC65105
0.5306	Remote Similarity	NPC43550
0.5302	Remote Similarity	NPC70809
0.529	Remote Similarity	NPC96641
0.529	Remote Similarity	NPC163183
0.527	Remote Similarity	NPC481081
0.5263	Remote Similarity	NPC112352
0.5245	Remote Similarity	NPC135904
0.5241	Remote Similarity	NPC481080
0.5217	Remote Similarity	NPC481079
0.5208	Remote Similarity	NPC191827
0.5205	Remote Similarity	NPC237191
0.5197	Remote Similarity	NPC293031
0.5188	Remote Similarity	NPC469946
0.5163	Remote Similarity	NPC110385
0.5161	Remote Similarity	NPC199457
0.5141	Remote Similarity	NPC60557
0.5141	Remote Similarity	NPC76972
0.5141	Remote Similarity	NPC469782
0.5141	Remote Similarity	NPC67857
0.5141	Remote Similarity	NPC204414
0.5133	Remote Similarity	NPC37860
0.5103	Remote Similarity	NPC471550
0.5098	Remote Similarity	NPC68767
0.5068	Remote Similarity	NPC110633
0.5066	Remote Similarity	NPC224381
0.5066	Remote Similarity	NPC220160
0.5065	Remote Similarity	NPC153673
0.5064	Remote Similarity	NPC275225
0.5059	Remote Similarity	NPC469778
0.5033	Remote Similarity	NPC144644
0.5033	Remote Similarity	NPC170407

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8129
0.1-0.2	988
0.2-0.3	33
0.3-0.4	0
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