NPASS Compound

Natural Product: NPC318618

Natural Product ID	NPC318618
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KWBPKUMWVXUSCA-QRLKJHJBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23304561
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 105111 0 0 0 0 0 0 0 0999 V2000 -3.6764 2.0954 -1.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1269 1.2778 0.1093 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1151 0.1863 -0.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6152 -0.7540 -1.2697 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2739 -1.2920 -0.7594 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3922 -0.1533 -0.3468 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9919 0.6237 0.6535 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1846 -0.6132 0.1482 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0782 -0.1586 -0.6163 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5894 -1.2849 -1.3217 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9928 -1.1209 -1.7300 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7621 -0.0364 -1.0671 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2344 -0.3762 -1.0998 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0891 0.8588 -1.2094 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5417 0.5659 -1.2669 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0222 -0.6996 -0.6653 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2056 -0.3724 0.2103 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0892 -1.3050 1.4110 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5689 -1.4029 1.6058 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1096 -1.4974 0.1648 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6500 -1.2846 0.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0789 -0.8728 1.3477 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5462 -0.8105 1.2650 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2309 0.2620 0.2804 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7968 0.6858 0.2190 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9246 1.4118 0.7586 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3655 -2.8796 -0.1459 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3049 1.0193 0.6583 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3190 1.8401 0.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1243 3.1570 0.9395 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8772 4.1650 0.8548 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9488 3.1092 1.6246 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4207 1.7985 1.5626 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5901 -1.6370 -1.7566 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5755 1.2485 -1.8922 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4350 -1.8431 -1.4168 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8307 -1.9455 -2.7459 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3937 0.6298 -0.4060 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3511 0.3199 0.5267 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4046 -0.4987 -0.1858 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3858 -1.0442 0.8342 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6539 -0.0252 1.9167 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1945 1.3466 1.5495 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9872 1.4757 0.9586 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3445 2.2245 2.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3572 1.8365 3.7009 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0472 0.0268 2.0802 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8134 -2.1806 1.3968 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1253 0.4114 -0.9952 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6977 1.6152 -2.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6056 2.4352 -0.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2328 3.0686 -1.1565 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5470 1.9107 0.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1522 -0.4126 0.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4908 -0.2566 -2.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5082 -1.8786 0.1513 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7438 -1.8788 -1.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1766 0.4575 -1.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5318 0.4773 -1.4069 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0392 -1.6654 -2.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5309 -2.1707 -0.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9755 -0.8645 -2.8389 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5556 -2.0995 -1.7345 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3906 -0.9408 -2.0651 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8221 1.6624 -0.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8034 1.3154 -2.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0935 1.4892 -0.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8750 0.5316 -2.3601 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1734 -0.6599 -0.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5452 -0.9187 2.3189 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4800 -2.3128 1.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2534 -0.5159 2.1376 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3126 -2.3393 2.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1511 -2.2777 -0.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4078 -1.6219 2.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3875 0.1160 1.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1101 -1.7877 1.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2375 -0.5017 2.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4253 0.6538 1.2822 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7609 1.7577 -0.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7970 1.4090 1.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6929 -3.4524 0.2651 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1969 1.6165 -0.2599 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3746 1.8432 1.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5362 1.4176 2.6319 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8121 -2.3846 -2.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4674 -2.1978 -1.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8170 -1.0795 -2.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9187 1.1134 -2.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5072 1.5255 -1.9606 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0582 2.1195 -1.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4921 -2.8258 -2.8543 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4051 -1.0210 -3.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9614 -1.9669 -3.4460 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9863 -0.2985 1.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0166 -1.2583 -0.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3043 -1.3628 0.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2282 -0.3907 2.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9552 1.7812 0.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2745 3.2982 2.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3232 1.9910 3.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6884 2.5464 3.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5358 -0.1352 1.2338 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2096 -2.2815 2.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5430 1.1180 -1.3354 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 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 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 20 27 1 0 17 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 16 34 1 0 12 35 1 0 4 36 1 0 36 37 1 0 3 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 43 45 1 0 45 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 7 2 1 0 25 9 1 0 24 12 1 0 21 13 1 0 20 16 1 0 33 28 1 0 44 39 1 0 1 50 1 0 1 51 1 0 1 52 1 0 2 53 1 0 3 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 0 9 59 1 0 10 60 1 0 10 61 1 0 11 62 1 0 11 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 17 69 1 0 18 70 1 0 18 71 1 0 19 72 1 0 19 73 1 0 21 74 1 0 22 75 1 0 22 76 1 0 23 77 1 0 23 78 1 0 25 79 1 0 25 80 1 0 26 81 1 0 27 82 1 0 29 83 1 0 33 84 1 0 33 85 1 0 34 86 1 0 34 87 1 0 34 88 1 0 35 89 1 0 35 90 1 0 35 91 1 0 37 92 1 0 37 93 1 0 37 94 1 0 39 95 1 0 40 96 1 0 41 97 1 0 42 98 1 0 43 99 1 0 45100 1 0 45101 1 0 46102 1 0 47103 1 0 48104 1 0 49105 1 0 M END

Standard InCHIKey	KWBPKUMWVXUSCA-QRLKJHJBSA-N
Standard InCHI	InChI=1S/C36H56O13/c1-18-31(49-32-30(41)29(40)28(39)25(16-37)48-32)24(44-4)14-27(46-18)47-20-5-9-33(2)22-6-10-34(3)21(19-13-26(38)45-17-19)8-12-36(34,43)23(22)7-11-35(33,42)15-20/h13,18,20-25,27-32,37,39-43H,5-12,14-17H2,1-4H3/t18-,20+,21?,22?,23?,24+,25-,27+,28-,29-,30-,31-,32+,33-,34-,35+,36+/m1/s1
SMILES	CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C)OC)OC7C(C(C(C(O7)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	696.37	Volume:	680.317 ? Van der Waals volume.
Dense:	1.024	LogP:	0.079 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.739 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.217 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	38.0
TPSA:	193.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.164	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.668	Fsp³:	0.917
MCE-18:	134.957 ? 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:	0.004	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.167 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.108	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.047	MDCK Permeability:	-5.159
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.744	30% Bioavailability (F30%):	0.964
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.999
Plasma Protein Binding (PPB):	64.815%	Volume Distribution (VD):	-0.325
Fu:	31.314% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.043	BCRP inhibitor:	0.001
BSEP inhibitor:	0.083

ADMET: Metabolism

CYP1A2-inhibitor:	0.345	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.985	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.851	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.643	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.886	CYP2C8-inhibitor:	0.0
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):

2.968

Half-life (T1/2):

4.193

ADMET: Toxicity

hERG Blockers:	0.293	hERG Blockers (10um):	0.529
Human Hepatotoxicity (H-HT):	0.823	Drug-induced Liver Injury (DILI):	0.249
AMES Toxicity:	0.909	Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.982	Skin Sensitization:	0.686
Carcinogencity:	0.478	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.22
Drug-induced Neurotoxicity:	0.141	Ototoxicity:	0.994
Hematotoxicity:	0.077	Drug-induced Nephrotoxicity:	0.14
Genotoxicity:	0.947	RPMI-8226 Immunitoxicity:	0.504
A549 Cytotoxicity:	0.219	Hek293 Cytotoxicity:	0.945
BCF:	0.528 ? 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:	3.597 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.57 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.156 ? 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
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18512	Periploca graeca	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18512	Periploca graeca	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18512	Periploca graeca	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11771	Strophanthus kombe	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18512	Periploca graeca	Species	Apocynaceae	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 NPC318618 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	15614
0.1-0.2	29042
0.2-0.3	4546
0.3-0.4	449
0.4-0.5	59
0.5-0.6	75
0.6-0.7	52
0.7-0.8	0
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8837	High Similarity	NPC146857
0.8488	Intermediate Similarity	NPC475629
0.8272	Intermediate Similarity	NPC84987
0.8172	Intermediate Similarity	NPC329675
0.8172	Intermediate Similarity	NPC194716
0.8161	Intermediate Similarity	NPC475556
0.8161	Intermediate Similarity	NPC311706
0.7802	Intermediate Similarity	NPC329986
0.7802	Intermediate Similarity	NPC140092
0.732	Intermediate Similarity	NPC475419
0.7294	Intermediate Similarity	NPC99728
0.7294	Intermediate Similarity	NPC87250
0.7294	Intermediate Similarity	NPC244402
0.7294	Intermediate Similarity	NPC50305
0.7126	Intermediate Similarity	NPC34390
0.703	Intermediate Similarity	NPC474423
0.6875	Remote Similarity	NPC247190
0.6832	Remote Similarity	NPC329784
0.6809	Remote Similarity	NPC32793
0.6809	Remote Similarity	NPC116075
0.68	Remote Similarity	NPC74259
0.6782	Remote Similarity	NPC158344
0.6782	Remote Similarity	NPC474418
0.6733	Remote Similarity	NPC474908
0.6667	Remote Similarity	NPC486143
0.6667	Remote Similarity	NPC486135
0.6667	Remote Similarity	NPC486142
0.6667	Remote Similarity	NPC486137
0.6667	Remote Similarity	NPC486149
0.6634	Remote Similarity	NPC120390
0.66	Remote Similarity	NPC329636
0.6598	Remote Similarity	NPC469749
0.6598	Remote Similarity	NPC232785
0.6598	Remote Similarity	NPC486139
0.6556	Remote Similarity	NPC157376
0.6556	Remote Similarity	NPC142066
0.6556	Remote Similarity	NPC603972
0.6374	Remote Similarity	NPC5311
0.6374	Remote Similarity	NPC77299
0.6374	Remote Similarity	NPC17896
0.6374	Remote Similarity	NPC469755
0.6374	Remote Similarity	NPC284406
0.6374	Remote Similarity	NPC480906
0.6374	Remote Similarity	NPC197707
0.6374	Remote Similarity	NPC251866
0.6364	Remote Similarity	NPC486146
0.6327	Remote Similarity	NPC125077
0.6304	Remote Similarity	NPC480914
0.63	Remote Similarity	NPC486138
0.63	Remote Similarity	NPC276838
0.6289	Remote Similarity	NPC486130
0.6275	Remote Similarity	NPC486144
0.6275	Remote Similarity	NPC486145
0.6275	Remote Similarity	NPC486147
0.6275	Remote Similarity	NPC486136
0.6275	Remote Similarity	NPC486148
0.6237	Remote Similarity	NPC77319
0.6237	Remote Similarity	NPC471351
0.6237	Remote Similarity	NPC180079
0.6237	Remote Similarity	NPC471355
0.6224	Remote Similarity	NPC486127
0.6061	Remote Similarity	NPC264336
0.6042	Remote Similarity	NPC480907
0.602	Remote Similarity	NPC236973
0.602	Remote Similarity	NPC32177
0.602	Remote Similarity	NPC469756
0.602	Remote Similarity	NPC275901
0.6	Remote Similarity	NPC59288
0.5962	Remote Similarity	NPC475590
0.596	Remote Similarity	NPC188234
0.596	Remote Similarity	NPC480910
0.596	Remote Similarity	NPC240070
0.596	Remote Similarity	NPC480909
0.596	Remote Similarity	NPC608063
0.5957	Remote Similarity	NPC243196
0.5943	Remote Similarity	NPC117445
0.5943	Remote Similarity	NPC308262
0.5943	Remote Similarity	NPC486134
0.5943	Remote Similarity	NPC486141
0.5922	Remote Similarity	NPC486132
0.5922	Remote Similarity	NPC486131
0.5918	Remote Similarity	NPC30483
0.5918	Remote Similarity	NPC470897
0.5914	Remote Similarity	NPC219085
0.5895	Remote Similarity	NPC146456
0.5888	Remote Similarity	NPC486150
0.5865	Remote Similarity	NPC486128
0.5859	Remote Similarity	NPC292467
0.5794	Remote Similarity	NPC486140
0.5789	Remote Similarity	NPC76572
0.5789	Remote Similarity	NPC193382
0.567	Remote Similarity	NPC483822
0.5638	Remote Similarity	NPC99620
0.5625	Remote Similarity	NPC10823
0.5612	Remote Similarity	NPC471354
0.5612	Remote Similarity	NPC27507
0.5596	Remote Similarity	NPC486133
0.5588	Remote Similarity	NPC231518
0.5588	Remote Similarity	NPC488944
0.5588	Remote Similarity	NPC610296
0.5534	Remote Similarity	NPC208193
0.5521	Remote Similarity	NPC6108
0.5521	Remote Similarity	NPC469750
0.5521	Remote Similarity	NPC89514
0.551	Remote Similarity	NPC9499
0.551	Remote Similarity	NPC471360
0.551	Remote Similarity	NPC469751
0.551	Remote Similarity	NPC471361
0.551	Remote Similarity	NPC86159
0.551	Remote Similarity	NPC469752
0.551	Remote Similarity	NPC469754
0.551	Remote Similarity	NPC70542
0.5487	Remote Similarity	NPC486152
0.5464	Remote Similarity	NPC84949
0.5464	Remote Similarity	NPC480562
0.5464	Remote Similarity	NPC74945
0.5464	Remote Similarity	NPC31354
0.5464	Remote Similarity	NPC69576
0.5421	Remote Similarity	NPC488943
0.5421	Remote Similarity	NPC488942
0.5417	Remote Similarity	NPC309034
0.5278	Remote Similarity	NPC479360
0.5278	Remote Similarity	NPC479359
0.5278	Remote Similarity	NPC488938
0.5278	Remote Similarity	NPC488937
0.5248	Remote Similarity	NPC72260
0.52	Remote Similarity	NPC484202
0.52	Remote Similarity	NPC305574
0.5185	Remote Similarity	NPC475219
0.5172	Remote Similarity	NPC97487
0.5155	Remote Similarity	NPC471633
0.5133	Remote Similarity	NPC488945
0.5133	Remote Similarity	NPC488946
0.5102	Remote Similarity	NPC196429
0.51	Remote Similarity	NPC484212
0.51	Remote Similarity	NPC83287
0.5094	Remote Similarity	NPC55532
0.5051	Remote Similarity	NPC480915
0.505	Remote Similarity	NPC471353
0.5048	Remote Similarity	NPC479353
0.5048	Remote Similarity	NPC479354
0.5046	Remote Similarity	NPC476221
0.5046	Remote Similarity	NPC477709

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC318618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6086
0.1-0.2	2950
0.2-0.3	95
0.3-0.4	6
0.4-0.5	6
0.5-0.6	6
0.6-0.7	1
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
0.6374	Remote Similarity	NPD7319	Approved
0.5588	Remote Similarity	NPD8033	Approved
0.5354	Remote Similarity	NPD7516	Pre-clinical
0.5248	Remote Similarity	NPD8294	Phase 4
0.51	Remote Similarity	NPD7327	Approved
0.51	Remote Similarity	NPD7328	Phase 4
0.5094	Remote Similarity	NPD8377	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