NPASS Compound

Natural Product: NPC480081

Natural Product ID	NPC480081
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LGOXIUCRKMEOAH-VFBWBQQKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44584188
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 110111 0 0 0 0 0 0 0 0999 V2000 14.5189 -0.5467 0.3579 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3519 0.2633 -0.8725 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9749 0.6639 -1.2766 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2021 1.5093 -0.3465 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8414 0.9467 0.9754 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9555 -0.2755 0.8777 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6407 0.0204 0.1737 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8103 1.0558 0.8597 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5308 1.3264 0.1076 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6419 0.1225 -0.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1662 -0.5116 1.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2858 0.1595 2.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8747 0.4629 1.7643 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5300 1.3021 0.6194 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9778 0.7006 -0.6228 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 -0.0075 -0.5030 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5843 0.8759 -0.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5110 1.1822 -0.6826 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8326 0.6953 -2.0206 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1269 -0.0785 -2.0212 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9790 -1.2575 -1.0693 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3198 -2.0001 -1.1225 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3308 -3.0588 -0.0553 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8257 -3.1224 0.2698 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2422 -1.7152 0.0009 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6129 -1.5728 -0.6069 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6930 -2.1390 0.2772 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0262 -1.9597 -0.4019 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3239 -0.5113 -0.6723 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3464 0.2492 0.6227 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6416 1.7085 0.3722 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9718 1.8593 -0.2884 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0550 1.2990 0.5757 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8973 0.3327 0.3102 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8118 0.0870 1.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.2129 0.4143 0.9569 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4084 1.0181 2.4120 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3514 1.7671 1.9199 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7584 2.6941 2.5460 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6419 2.2356 -0.4623 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3427 -1.1156 -0.8285 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7603 -0.7466 0.2038 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4226 2.3590 0.3801 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0321 -0.6584 1.9609 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4038 -1.2589 0.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9039 0.1302 1.1751 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6949 -1.1846 0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9314 1.2428 -0.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8703 -0.2485 -1.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4240 -0.2669 -1.5778 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0978 1.2462 -2.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8181 2.4415 -0.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2905 1.9404 -0.8493 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2253 1.7093 1.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6908 0.7264 1.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3959 -1.1200 0.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7092 -0.5839 1.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7897 0.2359 -0.9011 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0937 -0.9711 0.2080 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3820 2.0314 0.8155 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6487 0.8072 1.9122 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0301 2.2427 0.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8613 1.5840 -0.9463 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9051 0.3880 -0.8214 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3001 -0.6445 -0.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0591 -0.9658 1.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6313 -1.4716 0.8508 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7169 1.1186 2.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2109 -0.4960 3.0599 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5181 1.1062 2.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5850 1.9721 0.9703 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7315 0.0088 -1.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8958 1.5343 -1.3911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3916 -0.5135 -1.4783 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7638 -0.8522 0.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6678 1.3313 0.9962 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2479 1.8529 -0.2157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0234 1.5958 -2.6912 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0855 0.1142 -2.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2805 -0.4462 -3.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9320 0.5903 -1.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1494 -1.9143 -1.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5037 -2.4336 -2.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9162 -4.0198 -0.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7732 -2.6596 0.8294 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9533 -3.4690 1.3016 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3201 -3.8637 -0.4059 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2900 -1.1941 1.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5864 -2.0408 -1.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7440 -0.4659 -0.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4893 -3.2468 0.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6757 -1.7073 1.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8432 -2.3547 0.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9956 -2.4861 -1.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3360 -0.4749 -1.1721 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6355 -0.0527 -1.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3191 0.1900 1.0690 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1056 -0.1382 1.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6741 2.2555 1.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0229 1.4394 -1.3044 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2030 2.9535 -0.4038 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8830 -0.1980 -0.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7779 -0.9690 1.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4759 -0.1371 0.0469 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.9694 0.2324 1.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.2552 1.5036 0.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8151 2.3241 0.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1316 -1.3322 0.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2025 2.7516 -0.5010 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5995 -1.4525 2.2077 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 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 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 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 31 40 1 0 25 41 1 0 21 42 1 0 14 43 1 0 13 44 1 0 41 22 1 0 38 33 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 9 63 1 0 10 64 1 0 10 65 1 0 11 66 1 0 11 67 1 0 12 68 1 0 12 69 1 0 13 70 1 1 14 71 1 1 15 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 0 18 77 1 0 19 78 1 0 19 79 1 0 20 80 1 0 20 81 1 0 21 82 1 6 22 83 1 6 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 32100 1 0 32101 1 0 34102 1 0 35103 1 0 36104 1 0 36105 1 0 36106 1 0 40107 1 0 42108 1 0 43109 1 0 44110 1 0 M END

Standard InCHIKey	LGOXIUCRKMEOAH-VFBWBQQKSA-N
Standard InCHI	InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-17-22-33(39)34(40)23-18-12-13-19-24-35(41)36-26-25-32(44-36)21-16-14-15-20-31(38)28-30-27-29(2)43-37(30)42/h12-13,27,29,31-36,38-41H,3-11,14-26,28H2,1-2H3/b13-12-/t29?,31?,32?,33-,34-,35+,36+/m0/s1
SMILES	CCCCCCCCCCCC[C@@H]([C@H](CC/C=CCC[C@H]([C@H]1CCC(CCCCCC(CC2=CC(C)OC2=O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	622.48	Volume:	685.017 ? Van der Waals volume.
Dense:	0.909	LogP:	6.728 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.629 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.706 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	27.0	Rigid Bonds:	12.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.042	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.769	Fsp³:	0.865
MCE-18:	32.174 ? 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:	0
Colloidal aggregators:	0.705	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.059 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.031 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.579	Promiscuous compounds:	0.035

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.099	MDCK Permeability:	-4.757
Pgp-inhibitor:	0.0	Pgp-substrate:	0.007
PAMPA:	0.044 ? 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):	0.416
20% Bioavailability (F20%):	0.847	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.679
Plasma Protein Binding (PPB):	97.065%	Volume Distribution (VD):	0.506
Fu:	3.65% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.908
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.428
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.019	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.252	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.025	CYP2D6-substrate:	0.98
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.974
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.852
HLM stability:	0.265 ? 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):

6.206

Half-life (T1/2):

0.894

ADMET: Toxicity

hERG Blockers:	0.54	hERG Blockers (10um):	0.831
Human Hepatotoxicity (H-HT):	0.492	Drug-induced Liver Injury (DILI):	0.018
AMES Toxicity:	0.036	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.64	Skin Sensitization:	1.0
Carcinogencity:	0.037	Eye Corrosion:	0.004
Eye Irritation:	0.486	Respiratory Toxicity:	0.7
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.895
Hematotoxicity:	0.026	Drug-induced Nephrotoxicity:	0.87
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.889	Hek293 Cytotoxicity:	0.355
BCF:	1.27 ? 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:	5.044 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.199 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.214 ? 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
NPO40783	Annona coriaceae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778244]

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
ED50	2

Activity Type	# Activity
Cell line	2

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
NPT189	Cell line	Vero	Chlorocebus aethiops	ED50	=	5.7	10'-3 ug/ml	PMID[8778244]
NPT91	Cell line	KB	Homo sapiens	ED50	<	3.0	10'-7 ug/ml	PMID[8778244]

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 NPC480081 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	18110
0.1-0.2	29228
0.2-0.3	2194
0.3-0.4	96
0.4-0.5	36
0.5-0.6	77
0.6-0.7	78
0.7-0.8	0
0.8-0.85	4
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8929	High Similarity	NPC279267
0.8846	High Similarity	NPC473478
0.8846	High Similarity	NPC473651
0.8846	High Similarity	NPC66346
0.8679	High Similarity	NPC231096
0.8679	High Similarity	NPC475581
0.8679	High Similarity	NPC283085
0.8679	High Similarity	NPC62118
0.8679	High Similarity	NPC107717
0.8679	High Similarity	NPC488252
0.8333	Intermediate Similarity	NPC132496
0.8182	Intermediate Similarity	NPC480082
0.8	Intermediate Similarity	NPC606740
0.8	Intermediate Similarity	NPC608614
0.7963	Intermediate Similarity	NPC20621
0.7963	Intermediate Similarity	NPC318963
0.7963	Intermediate Similarity	NPC605101
0.7895	Intermediate Similarity	NPC91067
0.7759	Intermediate Similarity	NPC253801
0.7544	Intermediate Similarity	NPC233551
0.7544	Intermediate Similarity	NPC40376
0.7544	Intermediate Similarity	NPC21208
0.7407	Intermediate Similarity	NPC134865
0.7407	Intermediate Similarity	NPC488246
0.7407	Intermediate Similarity	NPC103523
0.7407	Intermediate Similarity	NPC488627
0.7407	Intermediate Similarity	NPC480080
0.7407	Intermediate Similarity	NPC488631
0.7368	Intermediate Similarity	NPC169511
0.7368	Intermediate Similarity	NPC287164
0.7368	Intermediate Similarity	NPC234077
0.7321	Intermediate Similarity	NPC488250
0.7288	Intermediate Similarity	NPC322529
0.7193	Intermediate Similarity	NPC69082
0.7193	Intermediate Similarity	NPC488249
0.7143	Intermediate Similarity	NPC65930
0.7018	Intermediate Similarity	NPC329615
0.6981	Remote Similarity	NPC606043
0.6852	Remote Similarity	NPC107986
0.6852	Remote Similarity	NPC223871
0.6852	Remote Similarity	NPC231009
0.6852	Remote Similarity	NPC103284
0.6852	Remote Similarity	NPC110710
0.6852	Remote Similarity	NPC1083
0.6852	Remote Similarity	NPC82795
0.6852	Remote Similarity	NPC286338
0.6852	Remote Similarity	NPC603931
0.6852	Remote Similarity	NPC604237
0.6825	Remote Similarity	NPC482766
0.6786	Remote Similarity	NPC477011
0.678	Remote Similarity	NPC488244
0.6727	Remote Similarity	NPC488253
0.6727	Remote Similarity	NPC473669
0.6727	Remote Similarity	NPC488251
0.6607	Remote Similarity	NPC81045
0.6607	Remote Similarity	NPC232555
0.6607	Remote Similarity	NPC39754
0.6607	Remote Similarity	NPC171135
0.6607	Remote Similarity	NPC171174
0.6607	Remote Similarity	NPC182383
0.6607	Remote Similarity	NPC114694
0.6607	Remote Similarity	NPC61257
0.6607	Remote Similarity	NPC320569
0.6607	Remote Similarity	NPC485248
0.6607	Remote Similarity	NPC133730
0.6607	Remote Similarity	NPC191929
0.6607	Remote Similarity	NPC142117
0.6607	Remote Similarity	NPC100454
0.6607	Remote Similarity	NPC242364
0.6607	Remote Similarity	NPC480249
0.6607	Remote Similarity	NPC172821
0.6607	Remote Similarity	NPC485249
0.6607	Remote Similarity	NPC274446
0.6607	Remote Similarity	NPC485251
0.6607	Remote Similarity	NPC151403
0.6607	Remote Similarity	NPC240695
0.6607	Remote Similarity	NPC261952
0.6607	Remote Similarity	NPC605171
0.6508	Remote Similarity	NPC473663
0.6508	Remote Similarity	NPC473723
0.6508	Remote Similarity	NPC475173
0.65	Remote Similarity	NPC258068
0.65	Remote Similarity	NPC476583
0.6491	Remote Similarity	NPC93794
0.6491	Remote Similarity	NPC488632
0.6491	Remote Similarity	NPC473504
0.6491	Remote Similarity	NPC81778
0.6491	Remote Similarity	NPC40066
0.6491	Remote Similarity	NPC47937
0.6452	Remote Similarity	NPC488630
0.6452	Remote Similarity	NPC488625
0.6452	Remote Similarity	NPC488626
0.6441	Remote Similarity	NPC602738
0.6379	Remote Similarity	NPC280621
0.6379	Remote Similarity	NPC48338
0.6379	Remote Similarity	NPC241360
0.6379	Remote Similarity	NPC293136
0.6379	Remote Similarity	NPC488628
0.6271	Remote Similarity	NPC178215
0.6271	Remote Similarity	NPC42598
0.6271	Remote Similarity	NPC473687
0.6271	Remote Similarity	NPC204686
0.6271	Remote Similarity	NPC219498
0.6271	Remote Similarity	NPC308412
0.6271	Remote Similarity	NPC134885
0.6271	Remote Similarity	NPC488247
0.6271	Remote Similarity	NPC210218
0.6271	Remote Similarity	NPC488248
0.6167	Remote Similarity	NPC309211
0.6154	Remote Similarity	NPC608138
0.6129	Remote Similarity	NPC488623
0.6129	Remote Similarity	NPC320458
0.6129	Remote Similarity	NPC488624
0.6129	Remote Similarity	NPC488629
0.6102	Remote Similarity	NPC480079
0.5968	Remote Similarity	NPC130359
0.5968	Remote Similarity	NPC14901
0.5965	Remote Similarity	NPC329829
0.5932	Remote Similarity	NPC607439
0.5902	Remote Similarity	NPC329838
0.5902	Remote Similarity	NPC134807
0.5893	Remote Similarity	NPC112685
0.5781	Remote Similarity	NPC239517
0.569	Remote Similarity	NPC100921
0.569	Remote Similarity	NPC475159
0.569	Remote Similarity	NPC131002
0.569	Remote Similarity	NPC473780
0.569	Remote Similarity	NPC477018
0.569	Remote Similarity	NPC604521
0.5667	Remote Similarity	NPC600524
0.5667	Remote Similarity	NPC608355
0.5625	Remote Similarity	NPC477014
0.5625	Remote Similarity	NPC477013
0.5574	Remote Similarity	NPC219652
0.5574	Remote Similarity	NPC473840
0.5556	Remote Similarity	NPC473707
0.5556	Remote Similarity	NPC20339
0.55	Remote Similarity	NPC156804
0.5484	Remote Similarity	NPC473904
0.5469	Remote Similarity	NPC473995
0.5455	Remote Similarity	NPC473520
0.5439	Remote Similarity	NPC73310
0.5439	Remote Similarity	NPC473529
0.5439	Remote Similarity	NPC180363
0.5439	Remote Similarity	NPC94875
0.5439	Remote Similarity	NPC11332
0.5439	Remote Similarity	NPC145914
0.5439	Remote Similarity	NPC601174
0.5439	Remote Similarity	NPC601403
0.5439	Remote Similarity	NPC603568
0.5439	Remote Similarity	NPC604330
0.5439	Remote Similarity	NPC608300
0.5439	Remote Similarity	NPC611200
0.5439	Remote Similarity	NPC611571
0.541	Remote Similarity	NPC473649
0.541	Remote Similarity	NPC473156
0.541	Remote Similarity	NPC154097
0.541	Remote Similarity	NPC163093
0.541	Remote Similarity	NPC159750
0.541	Remote Similarity	NPC73248
0.541	Remote Similarity	NPC282815
0.541	Remote Similarity	NPC470401
0.541	Remote Similarity	NPC600956
0.541	Remote Similarity	NPC610454
0.5397	Remote Similarity	NPC600188
0.5323	Remote Similarity	NPC473671
0.5323	Remote Similarity	NPC475268
0.5323	Remote Similarity	NPC470400
0.5323	Remote Similarity	NPC25703
0.5323	Remote Similarity	NPC77871
0.5323	Remote Similarity	NPC9678
0.5323	Remote Similarity	NPC319036
0.5323	Remote Similarity	NPC604764
0.5323	Remote Similarity	NPC605867
0.5312	Remote Similarity	NPC477012
0.5273	Remote Similarity	NPC609415
0.5238	Remote Similarity	NPC132940
0.5217	Remote Similarity	NPC488245
0.5167	Remote Similarity	NPC25764
0.5167	Remote Similarity	NPC235809
0.5167	Remote Similarity	NPC39279
0.5167	Remote Similarity	NPC39167
0.5167	Remote Similarity	NPC292809
0.5167	Remote Similarity	NPC202055
0.5167	Remote Similarity	NPC606804
0.5167	Remote Similarity	NPC607425
0.5167	Remote Similarity	NPC608574
0.5156	Remote Similarity	NPC20533
0.5156	Remote Similarity	NPC485250
0.5156	Remote Similarity	NPC477010
0.5143	Remote Similarity	NPC477017
0.5143	Remote Similarity	NPC477016

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6648
0.1-0.2	2446
0.2-0.3	56
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