NPASS Compound

Natural Product: NPC480443

Natural Product ID	NPC480443
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HWLQEFXGHDFIIL-BRLPPCAJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	127039669
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 110116 0 0 0 0 0 0 0 0999 V2000 0.7814 -12.2259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2814 -12.2259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6910 -12.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8400 -11.7747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5796 -10.2975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9200 -8.4854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 -7.1864 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 1.2709 -6.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1386 -6.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -4.8613 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 2.1595 -4.4101 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 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 3.4039 -4.7124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -3.8971 0.0000 C 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 7.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5905 3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -1.2990 0.0000 O 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 3.0000 -0.0000 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 3.0000 2.5981 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 1.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7500 -3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1491 -3.5623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -3.5623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -2.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5377 -1.1209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9472 -1.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2077 -3.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9577 -4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 -4.0753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4472 -1.6339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2877 0.1782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -0.7860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -6.3385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5209 -8.1506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0209 -10.7487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0796 -10.2975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5900 -13.0738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9410 -14.0379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7186 -12.2259 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7814 -13.7259 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7814 -10.7259 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0209 -13.7031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8400 -13.7031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2496 -11.2617 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8400 -8.8203 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9120 -8.9675 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3380 -6.8516 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4796 -7.5850 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2831 -5.6881 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8146 -7.4346 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -7.8157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7356 -5.5423 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2730 -2.8001 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -6.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4479 -2.2018 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9510 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9095 -0.5130 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4215 -1.4979 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3991 2.2632 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3991 0.3349 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2395 4.0753 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9095 3.1111 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2605 4.0753 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3300 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -7.7942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5706 -5.0602 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9270 -2.4224 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 -0.0238 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3858 -0.1994 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6172 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7077 -5.7092 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2567 -3.6601 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6586 -5.1601 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1972 -0.3349 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7765 0.3610 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2247 0.5948 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -7.6375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 -9.4496 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8296 -8.9985 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0900 -13.0738 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6910 -15.3370 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 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 29 32 1 0 23 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 22 43 1 0 20 44 1 0 12 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 50 52 1 0 49 53 1 0 48 54 1 0 47 55 1 0 11 56 1 0 10 57 1 0 6 58 1 0 5 59 1 0 4 60 1 0 3 61 1 0 58 2 1 0 14 9 1 0 35 16 2 0 41 36 1 0 52 46 1 0 33 19 1 0 30 25 1 0 1 62 1 0 1 63 1 0 1 64 1 0 2 65 1 1 3 66 1 6 4 67 1 1 5 68 1 1 6 69 1 6 8 70 1 0 8 71 1 0 9 72 1 1 10 73 1 1 11 74 1 1 12 75 1 6 13 76 1 1 21 77 1 0 24 78 1 0 24 79 1 0 26 80 1 0 26 81 1 0 27 82 1 0 27 83 1 0 28 84 1 0 28 85 1 0 29 86 1 0 32 87 1 0 37 88 1 0 38 89 1 0 40 90 1 0 41 91 1 0 42 92 1 0 43 93 1 0 44 94 1 0 46 95 1 1 47 96 1 6 48 97 1 6 49 98 1 1 50 99 1 6 51100 1 0 51101 1 0 51102 1 0 53103 1 0 54104 1 0 55105 1 0 56106 1 0 57107 1 0 59108 1 0 60109 1 0 61110 1 0 M END

Standard InCHIKey	HWLQEFXGHDFIIL-BRLPPCAJSA-N
Standard InCHI	InChI=1S/C39H49NO21/c1-13-23(45)27(49)30(52)37(56-13)55-12-21-25(47)29(51)35(61-38-31(53)28(50)24(46)14(2)57-38)39(58-21)60-34-26(48)22-20(44)10-19(43)17(11-40-9-3-4-18(42)36(40)54)33(22)59-32(34)15-5-7-16(41)8-6-15/h5-8,10,13-14,18,21,23-25,27-31,35,37-39,41-47,49-53H,3-4,9,11-12H2,1-2H3/t13-,14-,18?,21+,23-,24-,25-,27+,28+,29-,30+,31+,35+,37+,38-,39-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(c(CN4CCCC(C4=O)O)c3oc2c2ccc(cc2)O)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	867.28	Volume:	795.068 ? Van der Waals volume.
Dense:	1.091	LogP:	0.317 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.863 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.268 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	43.0
TPSA:	348.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	12.0	Rings:	7.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.096	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.752	Fsp³:	0.59
MCE-18:	177.032 ? 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:	0	PAINS Alert:	1
Colloidal aggregators:	0.582	Fluc inhibitor:	0.251 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.578 ? 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:	0.008	Promiscuous compounds:	0.069

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.568	MDCK Permeability:	-5.123
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.163
20% Bioavailability (F20%):	0.227	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.023
Plasma Protein Binding (PPB):	83.079%	Volume Distribution (VD):	-0.056
Fu:	16.192% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.031
BSEP inhibitor:	0.24

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.001 ? 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):

0.653

Half-life (T1/2):

5.88

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.284
Human Hepatotoxicity (H-HT):	0.299	Drug-induced Liver Injury (DILI):	0.61
AMES Toxicity:	0.724	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.024	Skin Sensitization:	0.938
Carcinogencity:	0.009	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.019
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.985
Hematotoxicity:	0.049	Drug-induced Nephrotoxicity:	0.231
Genotoxicity:	0.766	RPMI-8226 Immunitoxicity:	0.243
A549 Cytotoxicity:	0.2	Hek293 Cytotoxicity:	0.653
BCF:	0.384 ? 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:	3.056 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.901 ? 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
NPO40038	Astragalus monspessulanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26558405]

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
Activity	1

Activity Type	# Activity
Cell line	1

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
NPT984	Cell line	Hepatocyte	n.a.	Activity	=	177.0	%	PMID[26558405]

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 NPC480443 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	8665
0.1-0.2	36479
0.2-0.3	4157
0.3-0.4	345
0.4-0.5	142
0.5-0.6	52
0.6-0.7	10
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
0.9126	High Similarity	NPC480442
0.6857	Remote Similarity	NPC12013
0.6857	Remote Similarity	NPC11432
0.6857	Remote Similarity	NPC477613
0.6545	Remote Similarity	NPC602448
0.6455	Remote Similarity	NPC221342
0.6455	Remote Similarity	NPC476470
0.633	Remote Similarity	NPC122467
0.6273	Remote Similarity	NPC142142
0.6	Remote Similarity	NPC89052
0.6	Remote Similarity	NPC480445
0.5929	Remote Similarity	NPC89127
0.5847	Remote Similarity	NPC25523
0.5827	Remote Similarity	NPC473554
0.5794	Remote Similarity	NPC476215
0.5739	Remote Similarity	NPC292929
0.5714	Remote Similarity	NPC303694
0.5656	Remote Similarity	NPC488734
0.5656	Remote Similarity	NPC488735
0.5656	Remote Similarity	NPC488732
0.5656	Remote Similarity	NPC488738
0.5645	Remote Similarity	NPC480444
0.563	Remote Similarity	NPC173837
0.5586	Remote Similarity	NPC173582
0.5586	Remote Similarity	NPC265885
0.5586	Remote Similarity	NPC181465
0.5586	Remote Similarity	NPC215710
0.5586	Remote Similarity	NPC163242
0.5586	Remote Similarity	NPC272068
0.5586	Remote Similarity	NPC473438
0.5586	Remote Similarity	NPC253788
0.5565	Remote Similarity	NPC162394
0.5528	Remote Similarity	NPC488739
0.5505	Remote Similarity	NPC66087
0.5476	Remote Similarity	NPC209550
0.5476	Remote Similarity	NPC488737
0.5433	Remote Similarity	NPC192539
0.5385	Remote Similarity	NPC487499
0.5338	Remote Similarity	NPC487502
0.5328	Remote Similarity	NPC480441
0.5317	Remote Similarity	NPC488736
0.5317	Remote Similarity	NPC488733
0.5315	Remote Similarity	NPC95866
0.5197	Remote Similarity	NPC488740
0.5172	Remote Similarity	NPC240306
0.513	Remote Similarity	NPC203259
0.513	Remote Similarity	NPC65563
0.513	Remote Similarity	NPC33054
0.513	Remote Similarity	NPC470949
0.513	Remote Similarity	NPC155877
0.513	Remote Similarity	NPC176740
0.513	Remote Similarity	NPC471725
0.513	Remote Similarity	NPC134532
0.513	Remote Similarity	NPC602582
0.5089	Remote Similarity	NPC170052
0.5089	Remote Similarity	NPC135846
0.5086	Remote Similarity	NPC470444
0.5086	Remote Similarity	NPC473571
0.5086	Remote Similarity	NPC110941
0.5086	Remote Similarity	NPC186816
0.5082	Remote Similarity	NPC203145
0.5072	Remote Similarity	NPC487500
0.5036	Remote Similarity	NPC487501

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3516
0.1-0.2	5537
0.2-0.3	89
0.3-0.4	5
0.4-0.5	2
0.5-0.6	1
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
0.513	Remote Similarity	NPD6797	Phase 2

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