NPASS Compound

Natural Product: NPC289967

Natural Product ID	NPC289967
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PDIAXHCFRUNKBX-RWMGKXFKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581232
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 120124 0 0 0 0 0 0 0 0999 V2000 3.7500 -1.2990 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 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 O 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 -6.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8991 -5.5310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3086 -6.0440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5691 -7.5213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4200 -8.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0105 -7.9724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5691 -9.4496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3086 -10.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8667 -10.5134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4248 -10.0999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7467 -12.3176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8958 -13.2818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1678 -12.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5774 -11.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9869 -11.4608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8050 -11.0315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8193 -14.4638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3047 -14.2550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0319 -12.9431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2281 -15.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7136 -15.2283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6370 -16.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.1224 -16.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.0459 -17.3836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.4840 -18.7743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.9986 -18.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0751 -17.8011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4367 -20.3739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.9513 -20.5826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.4075 -19.9564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -19.5313 -17.1748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -20.4548 -18.3568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9079 -13.5612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5655 -14.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0618 -15.0140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7267 -16.1529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3842 -17.5011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5454 -18.7447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2030 -20.0928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3642 -21.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8679 -21.2318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2103 -19.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0491 -18.6400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7140 -19.7789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0564 -18.4307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0291 -22.4753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0218 -22.6846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1830 -23.9281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9786 -7.0082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5691 -4.5668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7500 -4.5668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 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 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 -2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 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 -6.5734 -4.6424 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7010 -5.9462 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3405 -7.0082 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6491 -4.2320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8086 -6.0440 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3191 -8.8203 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3780 -9.5644 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9190 -9.0143 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2806 -11.8941 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3458 -11.1419 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3463 -11.7801 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1010 -14.5539 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1321 -13.6359 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0643 -10.5643 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2584 -13.3104 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2474 -9.9836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6662 -16.8278 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.2755 -13.8375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.6844 -14.8108 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5897 -18.0098 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1601 -22.0680 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7426 -19.0972 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4659 -20.7914 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.8456 -21.3471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -21.6368 -17.4333 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -19.2728 -19.2803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -21.3783 -19.5388 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2303 -16.0483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8806 -17.6057 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6993 -20.1975 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3915 -17.2918 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7082 -19.0883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4046 -17.7732 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3988 -17.0826 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5327 -22.3707 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4265 -24.7669 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9394 -23.0894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3442 -25.1717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1277 -7.9724 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9786 -4.0538 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0105 -3.0896 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 3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0490 4.6471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5490 3.1471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.1962 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 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 19 18 1 1 19 20 1 0 20 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 36 41 1 0 35 42 1 0 42 43 1 0 22 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 53 55 1 0 55 56 1 0 52 57 1 0 51 58 1 0 58 59 1 0 15 60 1 0 14 61 1 0 13 62 1 0 5 63 2 0 63 64 1 0 64 65 2 0 65 66 1 0 64 67 1 0 67 68 1 0 65 3 1 0 17 12 1 0 27 19 1 0 38 33 1 0 54 49 1 0 1 69 1 0 1 70 1 0 1 71 1 0 4 72 1 0 6 73 1 0 7 74 1 0 11 75 1 0 11 76 1 0 12 77 1 6 13 78 1 1 14 79 1 6 15 80 1 1 16 81 1 1 20 82 1 0 20 83 1 0 21 84 1 0 22 85 1 6 23 86 1 1 24 87 1 6 25 88 1 0 25 89 1 0 26 90 1 0 31 91 1 0 32 92 1 0 34 93 1 0 38 94 1 0 40 95 1 0 40 96 1 0 40 97 1 0 41 98 1 0 43 99 1 0 43100 1 0 43101 1 0 47102 1 0 48103 1 0 50104 1 0 54105 1 0 56106 1 0 56107 1 0 56108 1 0 57109 1 0 59110 1 0 59111 1 0 59112 1 0 60113 1 0 61114 1 0 62115 1 0 63116 1 0 66117 1 0 68118 1 0 68119 1 0 68120 1 0 M END

Standard InCHIKey	PDIAXHCFRUNKBX-RWMGKXFKSA-N
Standard InCHI	InChI=1S/C45H52O23/c1-57-25-13-22(14-26(58-2)36(25)51)7-10-33(48)63-20-32-39(54)40(55)41(56)44(64-32)68-45(21-47)43(66-35(50)12-9-24-17-29(61-5)38(53)30(18-24)62-6)42(31(19-46)67-45)65-34(49)11-8-23-15-27(59-3)37(52)28(16-23)60-4/h7-18,31-32,39-44,46-47,51-56H,19-21H2,1-6H3/b10-7+,11-8+,12-9+/t31-,32-,39-,40+,41-,42-,43+,44-,45+/m1/s1
SMILES	COc1cc(/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@@]2(CO)[C@H]([C@@H]([C@@H](CO)O2)OC(=O)/C=C/c2cc(c(c(c2)OC)O)OC)OC(=O)/C=C/c2cc(c(c(c2)OC)O)OC)O)O)O)cc(c1O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	960.29	Volume:	906.722 ? Van der Waals volume.
Dense:	1.059	LogP:	1.755 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.985 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.407 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	35.0
TPSA:	323.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.044	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.453	Fsp³:	0.4
MCE-18:	134.714 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.884	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.214 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.651 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.115	Promiscuous compounds:	0.475

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.059	MDCK Permeability:	-5.574
Pgp-inhibitor:	0.108	Pgp-substrate:	0.311
PAMPA:	0.244 ? 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):	0.659
20% Bioavailability (F20%):	0.713	30% Bioavailability (F30%):	0.937
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.982
Plasma Protein Binding (PPB):	83.717%	Volume Distribution (VD):	-0.345
Fu:	18.295% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.965
BSEP inhibitor:	0.901

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.242
CYP2C9-inhibitor:	0.774	CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.201 ? 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):

1.539

Half-life (T1/2):

3.21

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.172
Human Hepatotoxicity (H-HT):	0.492	Drug-induced Liver Injury (DILI):	0.905
AMES Toxicity:	0.964	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.228	Skin Sensitization:	1.0
Carcinogencity:	0.337	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.018
Drug-induced Neurotoxicity:	0.414	Ototoxicity:	0.928
Hematotoxicity:	0.429	Drug-induced Nephrotoxicity:	0.984
Genotoxicity:	0.057	RPMI-8226 Immunitoxicity:	0.738
A549 Cytotoxicity:	0.952	Hek293 Cytotoxicity:	0.897
BCF:	0.506 ? 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:	3.499 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.946 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.309 ? 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
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24176362]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25466198]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7539	Raphanus sativus	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	5

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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	48920.0	nM	PMID[25466198]
NPT81	Cell line	A549	Homo sapiens	IC50	=	25870.0	nM	PMID[25466198]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	19250.0	nM	PMID[25466198]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	=	18550.0	nM	PMID[25466198]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	14060.0	nM	PMID[25466198]

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 NPC289967 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	16650
0.1-0.2	28903
0.2-0.3	3722
0.3-0.4	481
0.4-0.5	74
0.5-0.6	15
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9114	High Similarity	NPC472611
0.775	Intermediate Similarity	NPC90896
0.7722	Intermediate Similarity	NPC472612
0.7294	Intermediate Similarity	NPC283839
0.6667	Remote Similarity	NPC83743
0.6556	Remote Similarity	NPC173343
0.6341	Remote Similarity	NPC297342
0.6333	Remote Similarity	NPC300262
0.6207	Remote Similarity	NPC226005
0.618	Remote Similarity	NPC262182
0.5778	Remote Similarity	NPC471881
0.5699	Remote Similarity	NPC80732
0.5684	Remote Similarity	NPC125823
0.5684	Remote Similarity	NPC7145
0.5684	Remote Similarity	NPC143480
0.5604	Remote Similarity	NPC21516
0.5543	Remote Similarity	NPC186073
0.551	Remote Similarity	NPC201148
0.5393	Remote Similarity	NPC225307
0.5341	Remote Similarity	NPC219677
0.5306	Remote Similarity	NPC3460
0.5248	Remote Similarity	NPC28651
0.5204	Remote Similarity	NPC287615
0.5204	Remote Similarity	NPC199311
0.51	Remote Similarity	NPC481006

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC289967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5609
0.1-0.2	3478
0.2-0.3	61
0.3-0.4	1
0.4-0.5	1
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