NPASS Compound

Natural Product: NPC490344

Natural Product ID	NPC490344
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Procyanidin trimer EEC
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 101109 0 0 0 0 0 0 0 0999 V2000 7.7552 1.2340 -1.6415 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3726 1.1359 -1.6727 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8883 0.7946 -3.0773 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4160 0.7336 -3.0014 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8775 0.0742 -1.9209 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6980 -0.5006 -0.9652 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9686 0.0536 -0.7115 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0737 0.5443 0.6871 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6209 1.7534 1.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6934 2.1673 2.3552 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2220 1.3811 3.3652 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3017 1.8075 4.6875 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6667 0.1558 3.0355 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1839 -0.6524 4.0537 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5940 -0.2566 1.7111 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5027 -0.0206 -1.7807 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8419 -0.7097 -0.6405 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3730 -2.0739 -0.9889 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9273 -3.0457 -0.1248 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0878 -2.2857 -1.1022 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9027 -1.3552 -0.4390 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4605 -0.1787 0.1036 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 0.1546 0.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2848 1.3460 0.5773 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6267 1.6873 0.4963 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3964 2.1942 1.2068 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9396 1.8228 1.2705 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8813 2.6541 1.9018 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4011 0.6429 0.7287 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8456 0.2591 0.8032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6591 0.8739 -0.2832 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5419 -0.0671 -0.8632 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4358 2.0820 0.1038 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9527 2.0366 1.4135 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4417 1.2684 2.4275 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4147 0.3961 2.1511 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8839 -0.3946 3.1784 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8506 -1.2916 2.9670 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3877 -0.2984 4.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4299 0.5924 4.7188 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9227 0.6711 6.0230 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9549 1.3752 3.6995 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5913 2.2258 -0.8197 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5267 3.1332 -1.8538 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5566 3.3064 -2.7298 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7005 2.5594 -2.5886 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7503 2.7276 -3.4716 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8270 1.6285 -1.5670 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9690 0.8625 -1.4020 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7565 1.4937 -0.7101 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4019 -3.6669 -0.6246 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5582 -3.9373 0.7186 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8455 -5.1981 1.1966 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9899 -6.2573 0.3262 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2826 -7.5501 0.7901 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8355 -5.9966 -1.0187 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9824 -7.0703 -1.8927 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5483 -4.7334 -1.4893 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7061 0.5558 -2.7404 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3310 0.4671 -2.6104 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2549 1.2246 -3.8364 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6331 1.3168 -3.9721 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2625 1.9573 -5.0202 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1104 0.7555 -2.4371 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8733 2.1092 -1.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3518 -0.1501 -3.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2101 1.6626 -3.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7069 -0.7853 -0.8248 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0014 2.3987 0.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1288 3.1272 2.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2603 2.7981 4.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4116 -0.4601 5.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1529 -1.2254 1.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6684 -0.8314 0.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8384 -2.3255 -1.9898 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9162 -3.0451 -0.1893 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3964 -2.2457 -2.1789 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9136 2.5609 0.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7245 3.1246 1.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8964 2.6447 2.9296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8591 -0.8564 0.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9709 1.1615 -1.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7961 0.2648 -1.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8447 3.0203 0.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0903 -2.2951 2.9526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9841 -0.9090 5.2709 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7274 0.1266 6.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7594 2.0408 3.9774 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6255 3.7413 -1.9881 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4885 4.0194 -3.5308 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3088 3.5511 -3.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8703 1.3067 -1.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8061 0.7798 0.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4371 -3.0721 1.3857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9598 -5.3656 2.2584 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5338 -8.1544 1.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3521 -7.1148 -2.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4285 -4.5423 -2.5618 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3240 1.1860 -2.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6287 1.6733 -4.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7541 1.5153 -5.7713 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 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 1 0 13 15 2 0 5 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 24 26 2 0 26 27 1 0 27 28 1 0 27 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 37 39 2 0 39 40 1 0 40 41 1 0 40 42 2 0 33 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 46 48 1 0 48 49 1 0 48 50 2 0 20 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 54 55 1 0 54 56 1 0 56 57 1 0 56 58 2 0 16 59 2 0 59 60 1 0 59 61 1 0 61 62 2 0 62 63 1 0 7 2 1 0 15 8 1 0 23 17 1 0 36 30 1 0 50 43 1 0 58 51 1 0 62 4 1 0 29 22 1 0 42 35 1 0 1 64 1 0 2 65 1 1 3 66 1 0 3 67 1 0 7 68 1 1 9 69 1 0 10 70 1 0 12 71 1 0 14 72 1 0 15 73 1 0 17 74 1 0 18 75 1 6 19 76 1 0 20 77 1 6 25 78 1 0 26 79 1 0 28 80 1 0 30 81 1 0 31 82 1 6 32 83 1 0 33 84 1 1 38 85 1 0 39 86 1 0 41 87 1 0 42 88 1 0 44 89 1 0 45 90 1 0 47 91 1 0 49 92 1 0 50 93 1 0 52 94 1 0 53 95 1 0 55 96 1 0 57 97 1 0 58 98 1 0 60 99 1 0 61100 1 0 63101 1 0 M END

Standard InCHIKey	MOJZMWJRUKIQGL-GUZXBWELSA-N
Standard InCHI	InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37?,38?,39+,40+,41+,42+,43+/m0/s1
SMILES	O[C@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C(C1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3C1[C@@H](O)[C@H](OC3=C1C(O)=CC(O)=C3)C1=CC=C(O)C(O)=C1)C1=CC=C(O)C(O)=C1)=C(O)C=C2O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	866.21	Volume:	820.635 ? Van der Waals volume.
Dense:	1.056	LogP:	1.037 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.419 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.635 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	51.0
TPSA:	331.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	15.0	Rings:	9.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.355	Fsp³:	0.2
MCE-18:	193.333 ? 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:	0.854	Fluc inhibitor:	0.115 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.436 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.604 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.632	Promiscuous compounds:	0.128

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.81	MDCK Permeability:	-4.67
Pgp-inhibitor:	0.0	Pgp-substrate:	0.032
PAMPA:	0.053 ? 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):	0.0
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	87.815%	Volume Distribution (VD):	0.304
Fu:	16.279% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.023
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.03	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

7.038

Half-life (T1/2):

6.158

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.9
Human Hepatotoxicity (H-HT):	0.848	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.711	Rat Oral Acute Toxicity:	0.632
Maximum Recommended Daily Dose:	0.984	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.237	Respiratory Toxicity:	0.932
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.995
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.247
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.995
BCF:	1.179 ? 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:	3.775 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.782 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.234 ? 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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80Ã‚Â°N and longitude 4Ã‚Â°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-015-0761-z]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s12010-013-0354-4]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	DOI[10.1021/jf970571j]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/S-2006-958077]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1186/s40064-015-0831-z]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1501/Tarimbil_0000001065]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Leaves (mother plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Roots (runner plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	Suwon, Korea	2012-Nov	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Leaves	Suwon, Korea		DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Runners	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Leaves (runner plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Roots (mother plant)	Suwon, Korea	2011-Sep	DOI[10.7235/HORT.2013.12200]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[12232058]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13160012]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1453178]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568772]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18798681]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros AgrÃƒÂ³nomos de Albacete	2007	PMID[19256538]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21648406]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21648406]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[240326]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[3430165]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36838852]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446586]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38279238]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO366	Pyrus communis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5019	Mespilus germanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10339	Fragaria x ananassa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16230	Malus pumila	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[USDA]

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
NPO10339	Fragaria x ananassa	n.a.	Fruits	0.5	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO10339	Fragaria x ananassa	Raw	n.a.	0.5	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO14992	Prunus persica	Raw	n.a.	0.339999994	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO16230	Malus pumila	n.a.	n.a.	1.36500001	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO17024	Vitis vinifera	Raw	n.a.	0.129999995	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO25145	Cydonia oblonga	Other	n.a.	0.280000011	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO25145	Cydonia oblonga	n.a.	Fruits	0.28	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO29554	Diospyros kaki	Raw	n.a.	0.039999999	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO366	Pyrus communis	Raw	n.a.	0.014999999	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO366	Pyrus communis	n.a.	Fruits	0.015	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO4795	Prunus armeniaca	Raw	n.a.	0.01	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO4795	Prunus armeniaca	n.a.	Fruits	0.01	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO5019	Mespilus germanica	Other	n.a.	0.109999994	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO5019	Mespilus germanica	n.a.	Fruits	0.11	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO590	Malus domestica	n.a.	Fruits	1.365	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO7546	Prunus domestica	Raw	n.a.	7.730000178	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7546	Prunus domestica	n.a.	Fruits	7.73	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO9632	Annona reticulata	Raw	n.a.	0.970000029	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

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 NPC490344 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	21450
0.1-0.2	24893
0.2-0.3	3150
0.3-0.4	203
0.4-0.5	62
0.5-0.6	28
0.6-0.7	32
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246202
1.0	High Similarity	NPC224161
1.0	High Similarity	NPC46335
1.0	High Similarity	NPC279406
1.0	High Similarity	NPC486519
0.9821	High Similarity	NPC58190
0.9821	High Similarity	NPC108811
0.9821	High Similarity	NPC170103
0.9821	High Similarity	NPC236202
0.9821	High Similarity	NPC262911
0.9821	High Similarity	NPC202742
0.8594	High Similarity	NPC278548
0.8281	Intermediate Similarity	NPC226809
0.8167	Intermediate Similarity	NPC96576
0.8095	Intermediate Similarity	NPC313116
0.8095	Intermediate Similarity	NPC603340
0.7846	Intermediate Similarity	NPC70409
0.7846	Intermediate Similarity	NPC204770
0.7846	Intermediate Similarity	NPC600551
0.7846	Intermediate Similarity	NPC601980
0.7846	Intermediate Similarity	NPC602065
0.7846	Intermediate Similarity	NPC611024
0.7612	Intermediate Similarity	NPC600630
0.7612	Intermediate Similarity	NPC607896
0.7612	Intermediate Similarity	NPC611369
0.7568	Intermediate Similarity	NPC212614
0.7568	Intermediate Similarity	NPC205613
0.7534	Intermediate Similarity	NPC86630
0.75	Intermediate Similarity	NPC294558
0.75	Intermediate Similarity	NPC18185
0.75	Intermediate Similarity	NPC263940
0.75	Intermediate Similarity	NPC147743
0.75	Intermediate Similarity	NPC4809
0.75	Intermediate Similarity	NPC73517
0.7463	Intermediate Similarity	NPC211561
0.7432	Intermediate Similarity	NPC106601
0.7432	Intermediate Similarity	NPC151474
0.7167	Intermediate Similarity	NPC178054
0.7077	Intermediate Similarity	NPC601999
0.7051	Intermediate Similarity	NPC159526
0.6957	Remote Similarity	NPC601997
0.6957	Remote Similarity	NPC609211
0.6957	Remote Similarity	NPC610665
0.6897	Remote Similarity	NPC261619
0.6897	Remote Similarity	NPC61477
0.6897	Remote Similarity	NPC78770
0.6897	Remote Similarity	NPC219876
0.6897	Remote Similarity	NPC126029
0.6897	Remote Similarity	NPC15658
0.6761	Remote Similarity	NPC302549
0.6618	Remote Similarity	NPC184245
0.6618	Remote Similarity	NPC187801
0.6618	Remote Similarity	NPC610920
0.6575	Remote Similarity	NPC20050
0.6538	Remote Similarity	NPC78074
0.6486	Remote Similarity	NPC306267
0.64	Remote Similarity	NPC135021
0.6389	Remote Similarity	NPC272552
0.6389	Remote Similarity	NPC226108
0.6389	Remote Similarity	NPC322899
0.6364	Remote Similarity	NPC9309
0.6329	Remote Similarity	NPC478340
0.6301	Remote Similarity	NPC46283
0.6301	Remote Similarity	NPC469944
0.6267	Remote Similarity	NPC478616
0.6267	Remote Similarity	NPC478339
0.625	Remote Similarity	NPC478337
0.625	Remote Similarity	NPC478338
0.6216	Remote Similarity	NPC44192
0.6087	Remote Similarity	NPC277331
0.6087	Remote Similarity	NPC100482
0.6071	Remote Similarity	NPC478617
0.5867	Remote Similarity	NPC65333
0.5867	Remote Similarity	NPC134911
0.5857	Remote Similarity	NPC82917
0.5738	Remote Similarity	NPC207179
0.5738	Remote Similarity	NPC167571
0.5738	Remote Similarity	NPC278552
0.5696	Remote Similarity	NPC471404
0.5694	Remote Similarity	NPC165483
0.5663	Remote Similarity	NPC479793
0.5616	Remote Similarity	NPC28440
0.5541	Remote Similarity	NPC155564
0.5529	Remote Similarity	NPC479794
0.5484	Remote Similarity	NPC268266
0.5484	Remote Similarity	NPC42760
0.5484	Remote Similarity	NPC220825
0.5484	Remote Similarity	NPC268342
0.5373	Remote Similarity	NPC171932
0.5342	Remote Similarity	NPC20757
0.5342	Remote Similarity	NPC227516
0.5323	Remote Similarity	NPC601844
0.5147	Remote Similarity	NPC16435
0.5111	Remote Similarity	NPC185231
0.5075	Remote Similarity	NPC36835
0.5075	Remote Similarity	NPC246162
0.5075	Remote Similarity	NPC9743
0.5075	Remote Similarity	NPC260491
0.5075	Remote Similarity	NPC61506
0.5075	Remote Similarity	NPC240476

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC490344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4313
0.1-0.2	4765
0.2-0.3	63
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	2
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
0.6897	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1613	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