NPASS Compound

Natural Product: NPC478533

Natural Product ID	NPC478533
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MJTFJELPBFUYOV-NQVRDYSFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 2D 98105 0 0 0 0 0 0 0 0999 V2000 -3.3498 0.4244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8520 0.5062 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1740 1.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7062 2.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1328 3.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5593 3.6078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6741 2.6041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4086 3.6844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8351 3.2209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1470 1.7537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8192 -2.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1895 -1.4851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5599 -2.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5636 -0.9805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8136 0.3186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3463 0.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 1.4739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3463 -2.6982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9087 -3.1262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7041 -4.0201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5182 -4.1884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8946 -4.7846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0553 -1.1373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8099 -3.3942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5599 -4.6933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0153 -5.0562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8099 -5.9923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5599 -7.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8099 -8.5904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3099 -8.5904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5599 -7.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3099 -5.9923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6624 -3.5870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7079 -4.1971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9214 -3.3154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8647 -5.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3488 -6.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1921 -8.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1783 -8.6724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3918 -7.7908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2350 -6.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 1.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8173 0.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9419 0.4816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4410 0.5340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1128 5.0089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8264 0.1606 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1254 1.7083 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2680 -1.0734 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5457 2.4513 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3602 3.3326 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8466 4.6167 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0768 1.9786 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7888 1.6004 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6777 3.7188 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8137 1.3754 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6521 4.7451 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3342 3.2733 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0439 4.7063 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1111 2.9029 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8126 1.7019 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 -1.0037 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8578 -2.6401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4231 -1.3118 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1895 -2.9851 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9507 -2.6570 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2908 0.5789 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2523 1.7529 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9302 2.2689 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8437 -2.7878 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5798 -4.4677 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3305 -5.4728 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2710 -5.3808 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2984 -6.1610 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8062 -3.5934 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9370 0.0762 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0599 -7.2914 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5599 -9.8894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5599 -9.8894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9401 -7.2914 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1441 -5.0484 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5308 -5.6470 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1562 -9.2115 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3351 -10.1642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7621 -8.4009 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4485 -5.4173 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2439 0.0766 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7614 1.7058 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3538 -0.8864 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9225 0.7687 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8545 -0.9079 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7529 2.0012 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3179 6.2809 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 1 5 6 1 0 6 7 1 0 4 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 14 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 6 19 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 1 0 19 28 1 6 18 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 16 38 1 6 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 13 47 1 0 47 48 1 0 10 49 1 0 49 50 1 0 8 51 1 0 15 2 1 0 24 16 1 0 37 32 1 0 46 41 1 0 12 4 1 0 21 17 1 0 15 11 1 0 11 21 1 6 1 52 1 0 1 53 1 0 1 54 1 0 3 55 1 0 3 56 1 0 5 57 1 0 5 58 1 0 7 59 1 0 7 60 1 0 7 61 1 0 8 62 1 6 9 63 1 0 9 64 1 0 10 65 1 6 12 66 1 6 13 67 1 6 14 68 1 1 15 69 1 1 17 70 1 6 18 71 1 6 20 72 1 0 20 73 1 0 22 74 1 0 23 75 1 1 24 76 1 6 25 77 1 0 27 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 33 82 1 0 34 83 1 0 35 84 1 0 36 85 1 0 37 86 1 0 42 87 1 0 43 88 1 0 44 89 1 0 45 90 1 0 46 91 1 0 48 92 1 0 48 93 1 0 48 94 1 0 50 95 1 0 50 96 1 0 50 97 1 0 51 98 1 0 M END

Standard InCHIKey	MJTFJELPBFUYOV-NQVRDYSFSA-N
Standard InCHI	InChI=1S/C38H47NO12/c1-39-18-34(19-46-2)22(40)16-23(47-3)37-26(34)25(48-4)24(28(37)39)38(51-33(43)21-14-10-7-11-15-21)27-30(50-32(42)20-12-8-6-9-13-20)35(44,17-36(27,37)45)31(49-5)29(38)41/h6-15,22-31,40-41,44-45H,16-19H2,1-5H3/t22-,23+,24+,25+,26-,27+,28+,29+,30-,31+,34+,35-,36+,37-,38+/m1/s1
SMILES	CN1C[C@]2(COC)[C@@H](C[C@@H]([C@@]34[C@@H]2[C@H]([C@@H]([C@H]13)[C@@]1([C@H]2[C@H]([C@](C[C@@]42O)([C@H]([C@@H]1O)OC)O)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	709.31	Volume:	692.74 ? Van der Waals volume.
Dense:	1.024	LogP:	2.158 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.392 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.48 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	38.0
TPSA:	173.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	4.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.268	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.38	Fsp³:	0.632
MCE-18:	247.355 ? 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:	0.407	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.431

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.385	MDCK Permeability:	-5.058
Pgp-inhibitor:	0.263	Pgp-substrate:	0.963
PAMPA:	0.914 ? 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):	0.002
20% Bioavailability (F20%):	0.011	30% Bioavailability (F30%):	0.303
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047	MRP1:	0.99
Plasma Protein Binding (PPB):	75.958%	Volume Distribution (VD):	0.012
Fu:	23.405% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.168

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:	0.934	CYP3A4-substrate:	0.009
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.967
HLM stability:	0.916 ? 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):

7.304

Half-life (T1/2):

2.728

ADMET: Toxicity

hERG Blockers:	0.088	hERG Blockers (10um):	0.529
Human Hepatotoxicity (H-HT):	0.114	Drug-induced Liver Injury (DILI):	0.13
AMES Toxicity:	0.598	Rat Oral Acute Toxicity:	0.251
Maximum Recommended Daily Dose:	0.711	Skin Sensitization:	0.996
Carcinogencity:	0.394	Eye Corrosion:	0.001
Eye Irritation:	0.572	Respiratory Toxicity:	0.919
Drug-induced Neurotoxicity:	0.605	Ototoxicity:	0.601
Hematotoxicity:	0.408	Drug-induced Nephrotoxicity:	0.913
Genotoxicity:	0.204	RPMI-8226 Immunitoxicity:	0.179
A549 Cytotoxicity:	0.319	Hek293 Cytotoxicity:	0.541
BCF:	0.501 ? 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:	3.25 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.499 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.757 ? 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
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	tuber	n.a.	PMID[12913245]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1293938]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16181762]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22223386]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Lateral roots	n.a.	n.a.	PMID[22607495]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22628040]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22907155]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23225552]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23707213]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23707213]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24793215]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[27761113]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30892884]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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	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
NPT1635	Cell line	H9c2	Rattus norvegicus	IC50	>	100000.0	nM	PMID[30892884]

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 NPC478533 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	18269
0.1-0.2	30390
0.2-0.3	1146
0.3-0.4	25
0.4-0.5	7
0.5-0.6	10
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9241	High Similarity	NPC488589
0.8795	High Similarity	NPC478536
0.7079	Intermediate Similarity	NPC488583
0.7079	Intermediate Similarity	NPC478535
0.6667	Remote Similarity	NPC166521
0.6383	Remote Similarity	NPC184195
0.6383	Remote Similarity	NPC205
0.6186	Remote Similarity	NPC478539
0.617	Remote Similarity	NPC478534
0.6105	Remote Similarity	NPC478540
0.5918	Remote Similarity	NPC298772
0.5918	Remote Similarity	NPC108276
0.5918	Remote Similarity	NPC163578
0.5743	Remote Similarity	NPC478538
0.5556	Remote Similarity	NPC488604
0.5556	Remote Similarity	NPC281470
0.5392	Remote Similarity	NPC476495
0.5238	Remote Similarity	NPC94687
0.52	Remote Similarity	NPC478541
0.5049	Remote Similarity	NPC172769

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3617
0.1-0.2	5468
0.2-0.3	65
0.3-0.4	0
0.4-0.5	0
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