NPASS Compound

Natural Product: NPC306651

Natural Product ID	NPC306651
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AEYSUFUZZXZLEV-KBPCQMSISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	164508
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 106108 0 0 0 0 0 0 0 0999 V2000 -4.4540 3.6121 -2.8082 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1899 2.9655 -1.4629 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8006 1.5189 -1.6070 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9318 0.8068 -2.2898 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4379 0.8679 -0.2854 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2534 1.5213 0.3619 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5658 2.3974 -0.1869 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4700 3.2241 0.0039 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7808 4.4180 0.8880 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3790 5.3239 1.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1123 6.4621 2.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8399 5.9946 -0.1814 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8020 2.5709 0.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7813 2.5898 -0.2987 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0457 2.3770 -0.7397 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9324 1.9148 0.3528 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4862 0.8036 0.5023 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3773 -0.3102 -0.3877 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5175 -0.3038 -1.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8547 -0.3839 -0.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6470 -1.4835 -0.7006 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9016 -1.4503 -0.1163 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4199 -0.2758 0.3794 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6324 0.8461 0.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3827 0.8124 -0.3187 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6785 -0.2343 0.9670 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1544 -1.5839 0.2934 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0093 -1.8542 0.8048 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8451 -1.0422 0.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6851 -1.7825 0.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3844 -1.1814 0.1859 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6456 -3.1308 -0.1383 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7109 -4.0566 -0.1401 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1218 -5.3913 -0.5378 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3686 -5.1858 -0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5428 -3.7182 -0.6307 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8006 -3.2764 0.0644 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8598 -3.2158 -0.6249 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1861 -2.8467 -0.2791 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6693 -3.6470 0.8773 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0739 -3.3397 1.3367 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3209 -4.2944 2.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1178 -3.6382 0.3106 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3439 -1.3761 -0.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3723 -0.5448 -0.3660 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5698 -0.8175 0.1595 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8435 -2.9423 1.3975 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1434 -2.5213 0.4149 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1942 2.8659 1.3829 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8540 1.9083 1.6242 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8899 1.1285 1.6606 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5156 3.3944 -3.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7258 3.2759 -3.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4104 4.7285 -2.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3963 3.5250 -0.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0926 3.0709 -0.7906 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9289 1.4909 -2.3053 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9014 1.0708 -1.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7712 -0.2760 -2.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0136 1.2742 -3.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3170 1.1306 0.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2687 3.7255 -1.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1065 4.0377 1.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6179 5.0089 0.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2220 4.8643 1.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6814 7.1429 2.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5465 5.9441 2.9143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9995 6.9757 1.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4873 5.3406 -0.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4064 6.9144 0.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 6.3323 -0.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5582 3.3003 -1.1877 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0604 1.6194 -1.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4660 -0.1402 -1.0412 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3449 -1.1590 -2.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3572 0.6124 -2.0142 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3255 -2.4222 -1.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4896 -2.3554 -0.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0337 1.7710 0.6501 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8037 1.7226 -0.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8364 0.1473 1.8921 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9813 -0.1639 0.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5871 -0.7024 1.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2293 -4.1462 0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5512 -3.7694 -0.8367 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4083 -6.1870 0.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4975 -5.6343 -1.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8882 -5.6731 0.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7644 -5.7144 -1.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6546 -3.4203 -1.7020 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8643 -3.1058 -1.1764 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7057 -4.7147 0.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0271 -3.6332 1.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2211 -2.3447 1.7522 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4819 -4.2154 3.2482 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3742 -5.3277 2.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2298 -4.0043 3.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0718 -3.1163 0.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8554 -3.3138 -0.7165 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3685 -4.7272 0.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6397 -0.1853 0.9420 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3086 -2.1137 1.7510 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0177 -3.3820 0.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0138 2.8074 1.9581 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7567 1.8355 2.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6931 1.7834 2.4093 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 3 5 1 0 5 6 1 0 6 7 2 3 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 8 13 1 0 13 14 2 3 14 15 1 0 15 16 1 0 16 17 2 3 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 18 27 1 0 27 28 2 3 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 3 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 39 44 1 0 44 45 2 3 44 46 1 0 37 47 1 0 27 48 1 0 16 49 1 0 13 50 1 0 6 51 1 0 45 5 1 0 25 20 1 0 36 32 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 0 2 56 1 0 3 57 1 6 4 58 1 0 4 59 1 0 4 60 1 0 5 61 1 0 8 62 1 6 9 63 1 0 9 64 1 0 10 65 1 0 11 66 1 0 11 67 1 0 11 68 1 0 12 69 1 0 12 70 1 0 12 71 1 0 15 72 1 0 15 73 1 0 18 74 1 6 19 75 1 0 19 76 1 0 21 77 1 0 22 78 1 0 24 79 1 0 25 80 1 0 26 81 1 0 29 82 1 0 29 83 1 0 33 84 1 0 33 85 1 0 34 86 1 0 34 87 1 0 35 88 1 0 35 89 1 0 36 90 1 6 39 91 1 6 40 92 1 0 40 93 1 0 41 94 1 0 42 95 1 0 42 96 1 0 42 97 1 0 43 98 1 0 43 99 1 0 43100 1 0 46101 1 0 47102 1 0 48103 1 0 49104 1 0 50105 1 0 51106 1 0 M END

Standard InCHIKey	AEYSUFUZZXZLEV-KBPCQMSISA-N
Standard InCHI	InChI=1S/C36H55N7O8/c1-7-22(6)31-36(51)41-25(15-20(2)3)32(47)37-18-29(45)39-27(17-23-10-12-24(44)13-11-23)33(48)38-19-30(46)43-14-8-9-28(43)35(50)40-26(16-21(4)5)34(49)42-31/h10-13,20-22,25-28,31,44H,7-9,14-19H2,1-6H3,(H,37,47)(H,38,48)(H,39,45)(H,40,50)(H,41,51)(H,42,49)/t22-,25-,26-,27-,28-,31?/m0/s1
SMILES	CC[C@H](C)C1C(=N[C@@H](CC(C)C)C(=NCC(=N[C@@H](Cc2ccc(cc2)O)C(=NCC(=O)N2CCC[C@H]2C(=N[C@@H](CC(C)C)C(=N1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	713.41	Volume:	726.477 ? Van der Waals volume.
Dense:	0.982	LogP:	1.43 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.803 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.482 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	236.08 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	3.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.186	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.071	Fsp³:	0.639
MCE-18:	90.153 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.36	Fluc inhibitor:	0.215 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.863 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.469	MDCK Permeability:	-5.06
Pgp-inhibitor:	0.001	Pgp-substrate:	1.0
PAMPA:	0.993 ? 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):	0.917
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:	0.983
Plasma Protein Binding (PPB):	57.848%	Volume Distribution (VD):	-0.066
Fu:	43.51% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.931	BCRP inhibitor:	0.001
BSEP inhibitor:	0.392

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.015	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.152	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.142 ? 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):

0.745

Half-life (T1/2):

2.109

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.171	Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.986	Skin Sensitization:	1.0
Carcinogencity:	0.998	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.978
Drug-induced Neurotoxicity:	0.937	Ototoxicity:	0.999
Hematotoxicity:	0.076	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.354 ? 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:	3.292 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.916 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.909 ? 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
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[19157126]
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7673942]
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6715	Pseudostellaria heterophylla	Species	Caryophyllaceae	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 NPC306651 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	16745
0.1-0.2	31284
0.2-0.3	1357
0.3-0.4	344
0.4-0.5	91
0.5-0.6	32
0.6-0.7	6
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	Natural Product ID
0.6444	Remote Similarity	NPC262166
0.6364	Remote Similarity	NPC5194
0.631	Remote Similarity	NPC46427
0.6154	Remote Similarity	NPC261934
0.6146	Remote Similarity	NPC275110
0.6047	Remote Similarity	NPC252878
0.5905	Remote Similarity	NPC326349
0.5905	Remote Similarity	NPC323336
0.5806	Remote Similarity	NPC101679
0.5795	Remote Similarity	NPC485094
0.5778	Remote Similarity	NPC489556
0.5714	Remote Similarity	NPC486124
0.5618	Remote Similarity	NPC489829
0.5484	Remote Similarity	NPC56685
0.5426	Remote Similarity	NPC130309
0.5385	Remote Similarity	NPC479752
0.5361	Remote Similarity	NPC489827
0.534	Remote Similarity	NPC244509
0.5333	Remote Similarity	NPC202198
0.5333	Remote Similarity	NPC479068
0.5326	Remote Similarity	NPC479072
0.5312	Remote Similarity	NPC489825
0.5312	Remote Similarity	NPC489826
0.5312	Remote Similarity	NPC300315
0.5263	Remote Similarity	NPC487674
0.5263	Remote Similarity	NPC479074
0.5258	Remote Similarity	NPC141957
0.5258	Remote Similarity	NPC241794
0.5227	Remote Similarity	NPC242482
0.5208	Remote Similarity	NPC136797
0.5169	Remote Similarity	NPC224315
0.5146	Remote Similarity	NPC328649
0.5098	Remote Similarity	NPC483341
0.5094	Remote Similarity	NPC244336
0.5067	Remote Similarity	NPC118202
0.5052	Remote Similarity	NPC479070
0.5051	Remote Similarity	NPC479069
0.5042	Remote Similarity	NPC479140

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC306651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2948
0.1-0.2	5900
0.2-0.3	270
0.3-0.4	29
0.4-0.5	3
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