NPASS Compound

Natural Product: NPC505761

Natural Product ID	NPC505761
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dihydroxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-4,5-dihydroxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-7-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-4,5-dihydroxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-5-hydroxy-7-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 2D 114120 0 0 0 0 0 0 0 0999 V2000 -8.7286 4.1372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9786 2.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7181 1.3609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0586 -0.4512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 -1.7502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5586 -3.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 -2.0850 0.0000 O 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 -1.5000 -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 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 0.7500 -3.8971 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 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -6.4952 0.0000 O 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 5.2500 -3.8971 0.0000 O 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 1.5000 0.0000 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 2.5981 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 5.1962 0.0000 O 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 2.1595 7.0082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 8.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 9.4496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5209 10.7487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1386 8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 8.9366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 7.4594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1491 6.1603 0.0000 O 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 -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 -3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -4.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9895 -5.3743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -6.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3300 -7.1864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0695 -8.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3195 -9.9626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4305 -11.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2186 -9.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9686 -10.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6281 -9.1148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1281 -9.1148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 -7.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 -6.3385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 -5.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 -6.3385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2981 -4.5264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7981 -4.5264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 1.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4095 0.5130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9200 3.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8296 3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0796 5.1013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4786 5.4362 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0277 3.3872 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5307 5.0399 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3882 2.3251 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -0.1163 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6076 -2.5002 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8667 -1.3368 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9681 -3.5623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7395 -1.1209 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7388 -3.7143 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 5.5310 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 7.9724 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9200 11.0835 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4690 9.0345 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9721 10.6872 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2939 10.5467 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 12.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 10.2356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 7.9724 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 6.1603 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2345 4.0796 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4030 -3.3943 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0878 -6.0159 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3400 -8.1506 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9795 -9.2126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5174 -10.8654 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9305 -11.2617 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1956 -10.7248 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4574 -11.1097 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0667 -10.5492 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8781 -10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2981 -8.1506 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1274 -6.5214 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0070 -6.2530 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2252 -7.7804 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7367 -5.9609 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5481 -5.8255 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9160 2.6509 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8229 -0.9289 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 4.7665 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3340 4.6701 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8525 4.8994 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8296 6.4004 0.0000 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 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 1 0 18 20 2 0 12 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 24 36 2 0 36 37 1 0 37 38 1 0 37 39 2 0 39 40 1 0 40 41 2 0 9 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 42 55 1 0 55 56 1 0 55 57 1 0 57 58 1 0 4 59 1 0 59 60 1 0 59 61 1 0 61 62 1 0 61 63 1 0 63 64 1 0 63 2 1 0 57 7 1 0 40 11 1 0 53 44 1 0 20 13 1 0 39 22 1 0 34 26 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 6 4 69 1 1 6 70 1 0 6 71 1 0 7 72 1 6 9 73 1 6 14 74 1 0 15 75 1 0 17 76 1 0 19 77 1 0 20 78 1 0 23 79 1 0 26 80 1 6 28 81 1 1 29 82 1 0 29 83 1 0 29 84 1 0 30 85 1 6 31 86 1 0 32 87 1 1 33 88 1 0 34 89 1 6 35 90 1 0 36 91 1 0 38 92 1 0 42 93 1 1 44 94 1 1 46 95 1 1 47 96 1 0 47 97 1 0 48 98 1 0 49 99 1 6 50100 1 0 51101 1 1 52102 1 0 53103 1 6 54104 1 0 55105 1 6 56106 1 0 57107 1 1 58108 1 0 59109 1 1 60110 1 0 61111 1 6 62112 1 0 63113 1 1 64114 1 0 M END

Standard InCHIKey	CIWKSSSVUDYMTL-BTTUCDLLSA-N
Standard InCHI	InChI=1S/C39H50O25/c1-10-21(44)26(49)30(53)36(57-10)56-9-19-24(47)29(52)35(64-38-32(55)28(51)23(46)18(8-40)61-38)39(62-19)63-34-25(48)20-16(43)6-13(59-37-31(54)27(50)22(45)11(2)58-37)7-17(20)60-33(34)12-3-4-14(41)15(42)5-12/h3-7,10-11,18-19,21-24,26-32,35-47,49-55H,8-9H2,1-2H3/t10-,11-,18+,19+,21-,22-,23+,24+,26+,27+,28-,29-,30-,31-,32+,35+,36+,37-,38-,39-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(C4=CC=C(O)C(O)=C4)OC4=CC(O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]5O)=CC(O)=C4C3=O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.26	Volume:	821.869 ? Van der Waals volume.
Dense:	1.117	LogP:	-0.847 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.532 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.317 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	42.0
TPSA:	407.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	15.0	Rings:	7.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.08	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.953	Fsp³:	0.615
MCE-18:	185.381 ? 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:	0.649	Fluc inhibitor:	0.323 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.694 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.492 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.307	Promiscuous compounds:	0.599

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.05	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.0	Pgp-substrate:	0.948
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):	0.928
20% Bioavailability (F20%):	0.157	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	64.187%	Volume Distribution (VD):	-0.181
Fu:	30.962% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.013
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:	0.603
HLM stability:	0.003 ? 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):

0.164

Half-life (T1/2):

6.599

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.045
Human Hepatotoxicity (H-HT):	0.542	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.974	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.14	Drug-induced Nephrotoxicity:	0.913
Genotoxicity:	0.754	RPMI-8226 Immunitoxicity:	0.274
A549 Cytotoxicity:	0.901	Hek293 Cytotoxicity:	0.191
BCF:	0.379 ? 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:	2.977 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.718 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.763 ? 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
NPO48896	Warburgia ugandensis	Species	Canellaceae	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

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 NPC505761 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	24389
0.1-0.2	21071
0.2-0.3	3532
0.3-0.4	407
0.4-0.5	222
0.5-0.6	124
0.6-0.7	64
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC480441
0.8936	High Similarity	NPC25523
0.8125	Intermediate Similarity	NPC14187
0.7895	Intermediate Similarity	NPC142142
0.7789	Intermediate Similarity	NPC32641
0.7789	Intermediate Similarity	NPC256188
0.7789	Intermediate Similarity	NPC35119
0.7473	Intermediate Similarity	NPC605784
0.7423	Intermediate Similarity	NPC122467
0.73	Intermediate Similarity	NPC602448
0.7292	Intermediate Similarity	NPC186816
0.7216	Intermediate Similarity	NPC240306
0.6923	Remote Similarity	NPC136042
0.6848	Remote Similarity	NPC271692
0.68	Remote Similarity	NPC12013
0.68	Remote Similarity	NPC11432
0.68	Remote Similarity	NPC477613
0.6792	Remote Similarity	NPC303694
0.6765	Remote Similarity	NPC89127
0.6737	Remote Similarity	NPC116458
0.6737	Remote Similarity	NPC246943
0.6735	Remote Similarity	NPC67105
0.6701	Remote Similarity	NPC251417
0.6696	Remote Similarity	NPC192539
0.6667	Remote Similarity	NPC210073
0.6667	Remote Similarity	NPC155877
0.6667	Remote Similarity	NPC84362
0.6636	Remote Similarity	NPC298666
0.66	Remote Similarity	NPC115674
0.6574	Remote Similarity	NPC311850
0.6535	Remote Similarity	NPC64425
0.65	Remote Similarity	NPC203259
0.65	Remote Similarity	NPC33054
0.65	Remote Similarity	NPC176740
0.65	Remote Similarity	NPC471725
0.65	Remote Similarity	NPC134532
0.65	Remote Similarity	NPC156869
0.65	Remote Similarity	NPC602582
0.6486	Remote Similarity	NPC198199
0.6471	Remote Similarity	NPC470443
0.646	Remote Similarity	NPC209550
0.6442	Remote Similarity	NPC473071
0.6396	Remote Similarity	NPC68592
0.6381	Remote Similarity	NPC292929
0.6381	Remote Similarity	NPC221342
0.6381	Remote Similarity	NPC476470
0.6355	Remote Similarity	NPC89052
0.6316	Remote Similarity	NPC120952
0.6286	Remote Similarity	NPC473073
0.6277	Remote Similarity	NPC249281
0.6263	Remote Similarity	NPC254855
0.6263	Remote Similarity	NPC94610
0.6263	Remote Similarity	NPC95866
0.6239	Remote Similarity	NPC292019
0.6239	Remote Similarity	NPC202908
0.6214	Remote Similarity	NPC488073
0.6214	Remote Similarity	NPC126784
0.6214	Remote Similarity	NPC241423
0.6211	Remote Similarity	NPC297987
0.62	Remote Similarity	NPC8856
0.6162	Remote Similarity	NPC276377
0.6146	Remote Similarity	NPC46420
0.6105	Remote Similarity	NPC289667
0.6087	Remote Similarity	NPC480444
0.6078	Remote Similarity	NPC44931
0.6078	Remote Similarity	NPC275454
0.6078	Remote Similarity	NPC163242
0.6078	Remote Similarity	NPC272068
0.6078	Remote Similarity	NPC227508
0.6055	Remote Similarity	NPC11468
0.6042	Remote Similarity	NPC158674
0.6033	Remote Similarity	NPC223860
0.602	Remote Similarity	NPC611303
0.6019	Remote Similarity	NPC65003
0.6019	Remote Similarity	NPC150164
0.6	Remote Similarity	NPC162394
0.5962	Remote Similarity	NPC255157
0.5962	Remote Similarity	NPC259896
0.5938	Remote Similarity	NPC238376
0.5932	Remote Similarity	NPC262222
0.5932	Remote Similarity	NPC480442
0.5929	Remote Similarity	NPC488083
0.5922	Remote Similarity	NPC173582
0.5922	Remote Similarity	NPC265885
0.5922	Remote Similarity	NPC181465
0.5922	Remote Similarity	NPC215710
0.5922	Remote Similarity	NPC473438
0.5922	Remote Similarity	NPC253788
0.5917	Remote Similarity	NPC487499
0.5893	Remote Similarity	NPC473644
0.5876	Remote Similarity	NPC277205
0.5876	Remote Similarity	NPC37919
0.5872	Remote Similarity	NPC135358
0.5865	Remote Similarity	NPC22062
0.5865	Remote Similarity	NPC473634
0.5865	Remote Similarity	NPC138811
0.5825	Remote Similarity	NPC480466
0.5806	Remote Similarity	NPC249560
0.5804	Remote Similarity	NPC173837
0.5794	Remote Similarity	NPC209296
0.5773	Remote Similarity	NPC19709
0.5769	Remote Similarity	NPC39834
0.5766	Remote Similarity	NPC203145
0.5752	Remote Similarity	NPC164704
0.5726	Remote Similarity	NPC487502
0.5714	Remote Similarity	NPC65563
0.5714	Remote Similarity	NPC470949
0.5714	Remote Similarity	NPC189564
0.5714	Remote Similarity	NPC189142
0.5714	Remote Similarity	NPC77660
0.5701	Remote Similarity	NPC483414
0.5688	Remote Similarity	NPC195257
0.5688	Remote Similarity	NPC76831
0.5688	Remote Similarity	NPC220173
0.5686	Remote Similarity	NPC170052
0.5686	Remote Similarity	NPC476215
0.5686	Remote Similarity	NPC135846
0.566	Remote Similarity	NPC470444
0.5657	Remote Similarity	NPC27640
0.5648	Remote Similarity	NPC72016
0.5648	Remote Similarity	NPC473327
0.5641	Remote Similarity	NPC480445
0.5619	Remote Similarity	NPC67326
0.5614	Remote Similarity	NPC470715
0.5612	Remote Similarity	NPC127546
0.5612	Remote Similarity	NPC57625
0.5612	Remote Similarity	NPC173637
0.5612	Remote Similarity	NPC317489
0.5612	Remote Similarity	NPC223424
0.5612	Remote Similarity	NPC600591
0.5596	Remote Similarity	NPC486577
0.5593	Remote Similarity	NPC470719
0.5593	Remote Similarity	NPC488740
0.5583	Remote Similarity	NPC175429
0.5577	Remote Similarity	NPC473682
0.5566	Remote Similarity	NPC605592
0.5556	Remote Similarity	NPC145038
0.5556	Remote Similarity	NPC56077
0.5556	Remote Similarity	NPC281131
0.5556	Remote Similarity	NPC253662
0.5556	Remote Similarity	NPC65711
0.5556	Remote Similarity	NPC179950
0.5556	Remote Similarity	NPC88789
0.5556	Remote Similarity	NPC491374
0.5547	Remote Similarity	NPC487500
0.5545	Remote Similarity	NPC476472
0.5545	Remote Similarity	NPC294815
0.5545	Remote Similarity	NPC16194
0.5545	Remote Similarity	NPC488071
0.5526	Remote Similarity	NPC219043
0.5514	Remote Similarity	NPC473571
0.5514	Remote Similarity	NPC110941
0.5505	Remote Similarity	NPC606657
0.5504	Remote Similarity	NPC487501
0.5484	Remote Similarity	NPC473554
0.5472	Remote Similarity	NPC470405
0.5472	Remote Similarity	NPC471748
0.5462	Remote Similarity	NPC488736
0.5462	Remote Similarity	NPC488733
0.5462	Remote Similarity	NPC470717
0.5446	Remote Similarity	NPC59534
0.5439	Remote Similarity	NPC473072
0.5431	Remote Similarity	NPC277532
0.5424	Remote Similarity	NPC295625
0.5421	Remote Similarity	NPC479405
0.5421	Remote Similarity	NPC304741
0.5421	Remote Similarity	NPC303913
0.5405	Remote Similarity	NPC475382
0.5377	Remote Similarity	NPC29958
0.5372	Remote Similarity	NPC138990
0.5372	Remote Similarity	NPC488737
0.537	Remote Similarity	NPC479404
0.5357	Remote Similarity	NPC470445
0.5347	Remote Similarity	NPC305811
0.5333	Remote Similarity	NPC116864
0.5333	Remote Similarity	NPC244776
0.5333	Remote Similarity	NPC265115
0.5328	Remote Similarity	NPC480443
0.5323	Remote Similarity	NPC21359
0.5323	Remote Similarity	NPC460984
0.5321	Remote Similarity	NPC488074
0.531	Remote Similarity	NPC253685
0.53	Remote Similarity	NPC108831
0.53	Remote Similarity	NPC182634
0.5294	Remote Similarity	NPC488086
0.5294	Remote Similarity	NPC42773
0.5294	Remote Similarity	NPC45522
0.5294	Remote Similarity	NPC599850
0.5289	Remote Similarity	NPC470720
0.5273	Remote Similarity	NPC479403
0.5259	Remote Similarity	NPC48984
0.5254	Remote Similarity	NPC488087
0.5248	Remote Similarity	NPC323593
0.5248	Remote Similarity	NPC203500
0.5243	Remote Similarity	NPC285197
0.5217	Remote Similarity	NPC121703
0.52	Remote Similarity	NPC473043
0.52	Remote Similarity	NPC331652
0.5175	Remote Similarity	NPC470446
0.5172	Remote Similarity	NPC488075

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC505761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6020
0.1-0.2	3070
0.2-0.3	51
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
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
0.7449	Intermediate Similarity	NPD7251	Phase 2
0.65	Remote Similarity	NPD6797	Phase 2
0.6355	Remote Similarity	NPD7808	Phase 3
0.5794	Remote Similarity	NPD7054	Phase 4

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