NPASS Compound

Natural Product: NPC600188

Natural Product ID	NPC600188
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UXKFHZTYLKVREH-QCEKNMOOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501508
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 3D 108108 0 0 0 0 0 0 0 0999 V2000 12.4226 -3.3692 2.8629 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0938 -2.1869 1.9178 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4517 -2.6477 0.5418 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7428 -3.8067 0.0119 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3770 -3.8535 -0.4811 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2304 -3.2956 0.2586 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1436 -1.8093 0.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9826 -1.2395 1.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0344 0.2362 0.8283 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0231 1.0468 1.5346 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5977 0.7830 1.2582 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1733 0.9315 -0.1913 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4424 2.2534 -0.7353 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5649 3.0857 -1.1898 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1453 3.0767 -1.3340 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2592 1.9951 -0.9314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7931 2.3983 -1.2208 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4526 3.5410 -0.5731 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4579 2.2329 -2.6451 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0178 3.1934 -3.4982 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0186 2.0991 -2.9627 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7922 3.3013 -2.5567 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2468 3.2872 -2.8514 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0596 2.2252 -2.2018 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9891 2.3139 -0.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8789 1.2151 -0.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2600 1.5131 -0.6315 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6770 0.9569 -1.6120 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0522 2.5026 0.1042 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3963 2.6985 -0.4796 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2545 1.4812 -0.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4706 1.1032 1.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3853 -0.1380 1.0572 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6097 -0.4882 2.5012 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4711 -1.6847 2.6202 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8299 -2.9094 2.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6244 -3.1353 1.6499 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4650 -4.5597 1.2574 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1145 -4.5629 -0.2350 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6927 -5.1343 1.5340 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5576 -4.2035 2.0520 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7586 -4.3769 2.4199 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2974 -3.8929 2.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6492 -2.9862 3.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5352 -4.0308 2.8739 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7501 -1.3458 2.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0722 -1.9314 2.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4390 -1.7600 -0.1693 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5624 -2.9007 0.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4307 -4.3274 -0.7855 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7912 -4.6268 0.8535 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1664 -4.9683 -0.7111 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3424 -3.4503 -1.5831 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2796 -3.6897 -0.2002 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1766 -3.6575 1.3235 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0457 -1.2470 0.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7736 -1.5487 -0.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0559 -1.7182 0.6996 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2548 -1.4688 2.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1038 0.4300 -0.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0413 0.5626 1.2318 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1754 0.8567 2.6418 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2802 2.1208 1.3968 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9886 1.4993 1.8483 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2722 -0.2236 1.5724 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8279 0.1678 -0.7309 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1470 0.6161 -0.2471 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5513 2.5878 -0.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0716 4.0819 -1.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9686 3.2138 -2.4757 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6772 4.0529 -0.9358 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2738 1.7074 0.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4160 1.0795 -1.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2016 1.5692 -0.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6619 4.3796 -1.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9055 1.2552 -2.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3959 2.8026 -4.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3672 1.1638 -2.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0931 1.8723 -4.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3598 4.1762 -3.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5946 3.4700 -1.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6561 4.2771 -2.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3699 3.2011 -3.9536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1261 2.4092 -2.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8171 1.2031 -2.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9787 2.1213 -0.3314 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3977 3.2723 -0.3159 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9087 1.2741 0.9810 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6107 0.2200 -0.4697 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4877 3.4892 0.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0798 2.1498 1.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9692 3.5164 0.0587 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3230 3.1059 -1.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2457 1.6457 -0.9220 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7391 0.6248 -0.8810 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5384 0.8678 1.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0182 1.8853 1.5979 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9498 -0.8796 0.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3474 0.2512 0.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6113 -0.6045 2.9878 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0861 0.4173 2.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7872 -1.7835 3.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4008 -1.4808 2.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8276 -2.3735 1.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6264 -5.0209 1.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7095 -5.3294 -0.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0292 -4.8372 -0.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3277 -3.5836 -0.6904 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 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 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 2 0 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 41 42 2 0 41 36 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 0 14 69 1 0 15 70 1 0 15 71 1 0 16 72 1 0 16 73 1 0 17 74 1 1 18 75 1 0 19 76 1 6 20 77 1 0 21 78 1 0 21 79 1 0 22 80 1 0 22 81 1 0 23 82 1 0 23 83 1 0 24 84 1 0 24 85 1 0 25 86 1 0 25 87 1 0 26 88 1 0 26 89 1 0 29 90 1 0 29 91 1 0 30 92 1 0 30 93 1 0 31 94 1 0 31 95 1 0 32 96 1 0 32 97 1 0 33 98 1 0 33 99 1 0 34100 1 0 34101 1 0 35102 1 0 35103 1 0 37104 1 0 38105 1 1 39106 1 0 39107 1 0 39108 1 0 M END

Standard InCHIKey	UXKFHZTYLKVREH-QCEKNMOOSA-N
Standard InCHI	InChI=1S/C37H66O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-18-24-29-35(39)36(40)30-25-20-19-23-28-34(38)27-22-17-15-16-21-26-33-31-32(2)42-37(33)41/h14,18,31-32,35-36,39-40H,3-13,15-17,19-30H2,1-2H3/b18-14-/t32-,35+,36+/m0/s1
SMILES	CCCCCCCCCCCC/C=CCC[C@@H](O)[C@H](O)CCCCCCC(=O)CCCCCCCC1=C[C@H](C)OC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	590.49	Volume:	673.357 ? Van der Waals volume.
Dense:	0.877	LogP:	8.012 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.603 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.304 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	30.0	Rigid Bonds:	8.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.977	Fsp³:	0.838
MCE-18:	18.265 ? 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:	0.687	Fluc inhibitor:	0.26 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.133 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.711	Promiscuous compounds:	0.452

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.08	MDCK Permeability:	-4.778
Pgp-inhibitor:	0.024	Pgp-substrate:	0.015
PAMPA:	0.0 ? 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):	0.306
20% Bioavailability (F20%):	0.932	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.981
Plasma Protein Binding (PPB):	99.116%	Volume Distribution (VD):	0.806
Fu:	0.389% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.545
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.869
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.553	CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.036	CYP2D6-substrate:	0.988
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.609 ? 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):

4.959

Half-life (T1/2):

1.563

ADMET: Toxicity

hERG Blockers:	0.515	hERG Blockers (10um):	0.887
Human Hepatotoxicity (H-HT):	0.534	Drug-induced Liver Injury (DILI):	0.027
AMES Toxicity:	0.369	Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.89	Skin Sensitization:	1.0
Carcinogencity:	0.245	Eye Corrosion:	0.404
Eye Irritation:	0.816	Respiratory Toxicity:	0.851
Drug-induced Neurotoxicity:	0.041	Ototoxicity:	0.337
Hematotoxicity:	0.028	Drug-induced Nephrotoxicity:	0.934
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.1
A549 Cytotoxicity:	0.982	Hek293 Cytotoxicity:	0.447
BCF:	0.449 ? 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:	4.674 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.537 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.077 ? 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
NPO60487	Annona jahnii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	6

Activity Type	# Activity
Cell line	6

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
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	1.6	10'-2 ug/ml	PMID[10096871]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.8	ug ml-1	PMID[10096871]
NPT376	Cell line	A498	Homo sapiens	ED50	=	4.9	ug ml-1	PMID[10096871]
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[10096871]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	5.9	10'-2 ug/ml	PMID[10096871]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	2.3	10'-2 ug/ml	PMID[10096871]

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
-	Artemia	LC50	=	11.0	ug.mL-1	PMID[10096871]

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 NPC600188 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	16759
0.1-0.2	29061
0.2-0.3	3579
0.3-0.4	261
0.4-0.5	112
0.5-0.6	62
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8077	Intermediate Similarity	NPC488244
0.7174	Intermediate Similarity	NPC609415
0.6897	Remote Similarity	NPC253801
0.6792	Remote Similarity	NPC488246
0.6792	Remote Similarity	NPC144415
0.6792	Remote Similarity	NPC607439
0.6792	Remote Similarity	NPC608157
0.6667	Remote Similarity	NPC480082
0.6607	Remote Similarity	NPC477012
0.6441	Remote Similarity	NPC322529
0.6429	Remote Similarity	NPC605396
0.6226	Remote Similarity	NPC329829
0.6182	Remote Similarity	NPC480080
0.6087	Remote Similarity	NPC474705
0.5873	Remote Similarity	NPC488245
0.5862	Remote Similarity	NPC309211
0.5862	Remote Similarity	NPC477010
0.5806	Remote Similarity	NPC477015
0.5789	Remote Similarity	NPC219652
0.5789	Remote Similarity	NPC473840
0.569	Remote Similarity	NPC65930
0.566	Remote Similarity	NPC73310
0.566	Remote Similarity	NPC473529
0.566	Remote Similarity	NPC180363
0.566	Remote Similarity	NPC94875
0.566	Remote Similarity	NPC11332
0.566	Remote Similarity	NPC145914
0.566	Remote Similarity	NPC601174
0.566	Remote Similarity	NPC601403
0.566	Remote Similarity	NPC603568
0.566	Remote Similarity	NPC604330
0.566	Remote Similarity	NPC608300
0.566	Remote Similarity	NPC611200
0.566	Remote Similarity	NPC611571
0.5645	Remote Similarity	NPC280612
0.5593	Remote Similarity	NPC329838
0.5593	Remote Similarity	NPC329615
0.5517	Remote Similarity	NPC25703
0.5424	Remote Similarity	NPC473687
0.5424	Remote Similarity	NPC204686
0.5424	Remote Similarity	NPC219498
0.5424	Remote Similarity	NPC308412
0.5424	Remote Similarity	NPC134885
0.5424	Remote Similarity	NPC488247
0.5424	Remote Similarity	NPC210218
0.5424	Remote Similarity	NPC488248
0.5397	Remote Similarity	NPC480081
0.5357	Remote Similarity	NPC25764
0.5357	Remote Similarity	NPC235809
0.5357	Remote Similarity	NPC39279
0.5357	Remote Similarity	NPC475159
0.5357	Remote Similarity	NPC39167
0.5357	Remote Similarity	NPC131002
0.5357	Remote Similarity	NPC292809
0.5357	Remote Similarity	NPC202055
0.5357	Remote Similarity	NPC473780
0.5357	Remote Similarity	NPC604521
0.5357	Remote Similarity	NPC606804
0.5357	Remote Similarity	NPC607425
0.5357	Remote Similarity	NPC608574
0.5345	Remote Similarity	NPC600524
0.5345	Remote Similarity	NPC608355
0.5333	Remote Similarity	NPC134807
0.5333	Remote Similarity	NPC485250
0.5333	Remote Similarity	NPC488250
0.5246	Remote Similarity	NPC69082
0.5246	Remote Similarity	NPC488249
0.5172	Remote Similarity	NPC156804
0.5102	Remote Similarity	NPC218477
0.5085	Remote Similarity	NPC473156
0.5085	Remote Similarity	NPC163093
0.5085	Remote Similarity	NPC282815
0.5085	Remote Similarity	NPC600956
0.5077	Remote Similarity	NPC473905
0.5075	Remote Similarity	NPC477017
0.5075	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 NPC600188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6280
0.1-0.2	2763
0.2-0.3	103
0.3-0.4	3
0.4-0.5	1
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