NPASS Compound

Natural Product: NPC287695

Natural Product ID	NPC287695
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XIFRPUIQXADIQI-PHPFWZQASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102594774
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 2D 120130 0 0 0 0 0 0 0 0999 V2000 -2.3886 11.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 13.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 14.0594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0905 13.5464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1700 12.0692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 11.1050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7186 9.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6910 10.1408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8400 9.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5796 7.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7286 6.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4681 5.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0586 4.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0905 5.7092 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 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 -2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -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 -2.2500 -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 -0.0000 -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 -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 -3.8971 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 5.2500 -3.8971 0.0000 O 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 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1700 -4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 -5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 -4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 -3.6241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4681 -2.6600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -3.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -6.4004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1805 -7.3646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 -5.5525 0.0000 O 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 -4.5000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 0.0000 0.0000 O 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 -3.7500 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8991 4.8613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6386 6.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7877 7.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1972 6.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4577 5.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3086 4.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8672 4.7994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3463 7.7538 0.0000 O 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 -2.7395 6.6734 0.0000 O 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 0.1700 7.1864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 8.1506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7981 3.2678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1382 7.2483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8400 11.1050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0586 14.5106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7605 15.5366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5377 10.6538 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 13.6083 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6618 11.9125 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2186 9.6278 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2776 11.5827 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2496 8.6636 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7428 10.3746 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6172 4.2939 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7605 6.6734 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 -3.0000 0.0000 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 -1.8366 -5.3390 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 1.0866 -6.6381 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 6.2920 -2.8182 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 -1.9935 -2.1379 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5302 -1.9190 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0880 -3.7714 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4165 -6.5684 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -7.3646 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 -5.5525 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5327 -4.5057 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6616 -2.2759 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8777 -3.1730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 -7.8776 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0314 -8.3287 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9006 -7.0504 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8991 2.9329 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3951 7.1774 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5272 8.7799 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5691 2.8711 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1277 3.3222 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7558 7.2408 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 6.0350 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 7.6375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9554 5.5591 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6114 2.7548 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2872 6.2841 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3016 10.7676 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4681 13.9975 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6114 16.5008 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 1 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 29 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 42 49 1 0 41 50 1 0 29 51 1 0 25 52 1 0 23 53 1 0 20 54 2 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 2 0 58 59 1 0 59 60 2 0 60 61 1 0 61 62 2 0 61 63 1 0 60 64 1 0 56 65 1 0 65 66 1 0 17 67 1 0 14 68 2 0 68 69 1 0 13 70 1 0 11 71 1 0 8 72 1 0 4 73 1 0 3 74 1 0 6 1 1 0 69 7 1 0 68 10 1 0 65 15 1 0 54 16 1 0 62 57 1 0 51 19 1 0 38 21 1 0 47 40 1 0 27 22 1 0 35 30 1 0 1 75 1 0 2 76 1 0 5 77 1 0 7 78 1 1 8 79 1 1 9 80 1 0 9 81 1 0 12 82 1 0 15 83 1 0 18 84 1 0 21 85 1 6 24 86 1 0 26 87 1 0 31 88 1 0 32 89 1 0 35 90 1 0 36 91 1 0 37 92 1 0 38 93 1 1 40 94 1 1 41 95 1 6 42 96 1 1 43 97 1 1 44 98 1 1 45 99 1 0 45100 1 0 46101 1 0 48102 1 0 49103 1 0 50104 1 0 52105 1 0 53106 1 0 56107 1 1 58108 1 0 59109 1 0 62110 1 0 63111 1 0 64112 1 0 65113 1 1 66114 1 0 67115 1 0 70116 1 0 71117 1 0 72118 1 0 73119 1 0 74120 1 0 M END

Standard InCHIKey	XIFRPUIQXADIQI-PHPFWZQASA-N
Standard InCHI	InChI=1S/C51H46O23/c52-15-34-41(65)43(67)44(68)50(69-34)72-49-40-35-28(61)10-19(53)11-32(35)73-51(49,18-3-6-23(56)27(60)9-18)74-33-14-30(63)37-39(42(66)46(71-48(37)38(33)40)17-2-5-22(55)26(59)8-17)36-29(62)13-24(57)20-12-31(64)45(70-47(20)36)16-1-4-21(54)25(58)7-16/h1-11,13-14,31,34,39-46,49-50,52-68H,12,15H2/t31-,34-,39?,40+,41+,42-,43+,44-,45-,46-,49-,50+,51+/m1/s1
SMILES	c1cc(c(cc1[C@@H]1[C@@H](Cc2c(cc(c(C3c4c(cc5c([C@@H]6c7c(cc(cc7O[C@](c7ccc(c(c7)O)O)([C@@H]6O[C@H]6[C@@H]([C@H]([C@H]([C@@H](CO)O6)O)O)O)O5)O)O)c4O[C@H](c4ccc(c(c4)O)O)[C@@H]3O)O)c2O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1026.24	Volume:	951.25 ? Van der Waals volume.
Dense:	1.079	LogP:	0.819 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.174 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.856 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	60.0
TPSA:	399.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	17.0	Rings:	11.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.102	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.975	Fsp³:	0.294
MCE-18:	243.121 ? 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:	0.759	Fluc inhibitor:	0.014 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.434 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.643 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.572	Promiscuous compounds:	0.136

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.664	MDCK Permeability:	-4.389
Pgp-inhibitor:	0.0	Pgp-substrate:	0.598
PAMPA:	0.908 ? 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:	0.992
Plasma Protein Binding (PPB):	88.011%	Volume Distribution (VD):	0.118
Fu:	12.083% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.018
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	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):

4.093

Half-life (T1/2):

7.795

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.761
Human Hepatotoxicity (H-HT):	0.846	Drug-induced Liver Injury (DILI):	0.916
AMES Toxicity:	0.773	Rat Oral Acute Toxicity:	0.344
Maximum Recommended Daily Dose:	0.766	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.515
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.021	Drug-induced Nephrotoxicity:	0.228
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.08
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.995
BCF:	0.922 ? 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:	3.674 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.243 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.442 ? 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
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)00169-2]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15128023]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC287695 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	26174
0.1-0.2	20817
0.2-0.3	2597
0.3-0.4	174
0.4-0.5	40
0.5-0.6	48
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8764	High Similarity	NPC185231
0.6702	Remote Similarity	NPC147743
0.6702	Remote Similarity	NPC4809
0.6702	Remote Similarity	NPC73517
0.6392	Remote Similarity	NPC86630
0.6238	Remote Similarity	NPC159526
0.6	Remote Similarity	NPC106601
0.6	Remote Similarity	NPC151474
0.5955	Remote Similarity	NPC58190
0.5955	Remote Similarity	NPC108811
0.5955	Remote Similarity	NPC170103
0.5955	Remote Similarity	NPC236202
0.5955	Remote Similarity	NPC262911
0.5955	Remote Similarity	NPC202742
0.5941	Remote Similarity	NPC212614
0.5941	Remote Similarity	NPC205613
0.5889	Remote Similarity	NPC246202
0.5889	Remote Similarity	NPC224161
0.5889	Remote Similarity	NPC46335
0.5889	Remote Similarity	NPC279406
0.5889	Remote Similarity	NPC486519
0.5833	Remote Similarity	NPC20050
0.5784	Remote Similarity	NPC478337
0.5784	Remote Similarity	NPC478338
0.5686	Remote Similarity	NPC478340
0.5625	Remote Similarity	NPC278548
0.5612	Remote Similarity	NPC306267
0.5612	Remote Similarity	NPC478616
0.5612	Remote Similarity	NPC478339
0.5534	Remote Similarity	NPC78074
0.5521	Remote Similarity	NPC272552
0.5521	Remote Similarity	NPC226108
0.5521	Remote Similarity	NPC322899
0.5514	Remote Similarity	NPC478617
0.5347	Remote Similarity	NPC471404
0.5312	Remote Similarity	NPC70409
0.5312	Remote Similarity	NPC204770
0.5312	Remote Similarity	NPC600551
0.5312	Remote Similarity	NPC601980
0.5312	Remote Similarity	NPC602065
0.5312	Remote Similarity	NPC611024
0.5306	Remote Similarity	NPC46283
0.5306	Remote Similarity	NPC469944
0.5306	Remote Similarity	NPC134911
0.5263	Remote Similarity	NPC313116
0.5263	Remote Similarity	NPC603340
0.5258	Remote Similarity	NPC226809
0.5253	Remote Similarity	NPC44192
0.5102	Remote Similarity	NPC211561
0.5096	Remote Similarity	NPC9309
0.5054	Remote Similarity	NPC96576
0.5052	Remote Similarity	NPC160156
0.5052	Remote Similarity	NPC92565
0.5051	Remote Similarity	NPC600630
0.5051	Remote Similarity	NPC607896
0.5051	Remote Similarity	NPC611369

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC287695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6411
0.1-0.2	2680
0.2-0.3	54
0.3-0.4	3
0.4-0.5	2
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