NPASS Compound

Natural Product: NPC600880

Natural Product ID	NPC600880
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JJOWBVSGDGLUKQ-SBFMVFAKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507802
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 91 95 0 0 0 0 0 0 0 0999 V2000 6.7681 2.5460 -0.4244 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8228 1.8028 0.8926 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5175 2.6278 1.9366 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4398 1.4477 1.2708 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8880 1.8471 2.3308 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7026 0.6474 0.4463 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3521 0.2333 0.7042 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2628 -1.2223 0.9820 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1431 -2.1328 -0.1888 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5081 -2.7803 -0.4989 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2963 -3.3300 0.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5822 -1.4842 -1.4073 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7433 -0.2752 -1.1634 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3371 -0.5109 -0.7728 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2765 -1.6458 -1.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6827 -2.0140 -0.7444 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3987 -0.8873 -0.1562 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9253 -0.9652 -0.2407 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4703 -0.9116 -1.6194 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4085 -2.2859 0.3391 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6774 -2.1865 1.8359 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8939 -1.3116 1.9467 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8757 -1.6088 2.5827 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7883 -0.0148 1.1891 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9453 1.0573 2.2833 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8748 0.1930 0.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3971 0.1103 0.6805 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0947 1.4700 0.1044 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5958 1.6064 0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8784 0.4549 -0.5258 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9123 0.6208 -2.0305 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4222 0.5793 -0.0429 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2884 0.5199 1.4397 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2270 1.8709 -0.4422 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6031 1.8361 0.2086 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4804 0.7672 -0.3933 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3530 1.5221 -1.3768 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1057 2.7456 -1.6405 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4232 0.9752 -2.0255 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7486 2.9569 -0.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4334 3.4557 -0.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1260 1.9359 -1.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3630 0.8373 0.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6236 2.5370 1.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3580 2.2756 2.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2863 3.7080 1.7972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1195 0.7326 1.6981 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4822 -1.4472 1.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2314 -1.4933 1.5100 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4502 -3.0817 -1.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3298 -2.0635 -0.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6928 -3.6437 0.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9056 -4.0087 0.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9218 -3.8595 -0.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4516 -2.9140 0.8864 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1430 -2.1448 -2.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5042 -1.0872 -1.9605 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6206 0.1708 -2.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3545 -2.3637 -1.6248 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1836 -2.5162 -1.6011 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5791 -2.8558 0.0057 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2756 -1.0195 0.9673 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5192 0.0414 -2.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0240 -1.7559 -2.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5512 -1.2478 -1.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7462 -3.1255 0.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3925 -2.5392 -0.1132 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8251 -1.8231 2.4065 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9766 -3.2056 2.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7087 0.7077 3.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9623 1.1743 2.7964 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2615 2.0146 1.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4099 -0.7371 -0.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5087 0.7785 -0.6771 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6972 0.8459 0.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7458 0.0463 1.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4851 2.2148 0.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5848 1.6715 -0.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3769 2.5192 -0.5504 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2564 1.8830 1.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9243 0.8863 -2.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1990 -0.2841 -2.5799 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5945 1.4341 -2.3537 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2815 1.5653 1.9023 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0752 0.0274 2.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6618 0.0297 1.7393 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4036 2.0490 -1.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3318 2.7119 0.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5964 1.7510 1.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0176 2.8788 0.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9009 1.4623 -2.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 9 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 30 32 1 0 32 33 1 1 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 6 37 38 2 0 37 39 1 0 36 7 1 0 36 13 1 0 32 14 1 0 30 17 1 0 27 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 3 44 1 0 3 45 1 0 3 46 1 0 7 47 1 1 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 11 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 12 57 1 0 13 58 1 6 15 59 1 0 16 60 1 0 16 61 1 0 17 62 1 1 19 63 1 0 19 64 1 0 19 65 1 0 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 1 28 77 1 0 28 78 1 0 29 79 1 0 29 80 1 0 31 81 1 0 31 82 1 0 31 83 1 0 33 84 1 0 33 85 1 0 33 86 1 0 34 87 1 0 34 88 1 0 35 89 1 0 35 90 1 0 39 91 1 0 M END

Standard InCHIKey	JJOWBVSGDGLUKQ-SBFMVFAKSA-N
Standard InCHI	InChI=1S/C34H52O5/c1-20(2)27(36)39-26-19-29(3,4)18-22-21-10-11-24-31(7)14-13-25(35)30(5,6)23(31)12-15-33(24,9)32(21,8)16-17-34(22,26)28(37)38/h10,20,22-24,26H,11-19H2,1-9H3,(H,37,38)/t22-,23-,24+,26+,31-,32+,33+,34-/m0/s1
SMILES	CC(C)C(=O)O[C@@H]1CC(C)(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]12C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	540.38	Volume:	587.243 ? Van der Waals volume.
Dense:	0.92	LogP:	4.768 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.761 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.735 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	29.0
TPSA:	80.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.294	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.907	Fsp³:	0.853
MCE-18:	109.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.937	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.396	Promiscuous compounds:	0.026

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.365	MDCK Permeability:	-4.912
Pgp-inhibitor:	0.164	Pgp-substrate:	0.0
PAMPA:	0.996 ? 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):	0.0
20% Bioavailability (F20%):	0.056	30% Bioavailability (F30%):	0.009
50% Bioavailability (F50%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059	MRP1:	0.997
Plasma Protein Binding (PPB):	95.714%	Volume Distribution (VD):	-0.022
Fu:	3.937% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.537	BCRP inhibitor:	0.079
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.995	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.632	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.918
HLM stability:	0.993 ? 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):

5.263

Half-life (T1/2):

0.609

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.627	Drug-induced Liver Injury (DILI):	0.679
AMES Toxicity:	0.172	Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.36	Skin Sensitization:	0.84
Carcinogencity:	0.787	Eye Corrosion:	0.026
Eye Irritation:	0.132	Respiratory Toxicity:	0.635
Drug-induced Neurotoxicity:	0.05	Ototoxicity:	0.633
Hematotoxicity:	0.805	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.897	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.07	Hek293 Cytotoxicity:	0.093
BCF:	1.181 ? 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:	4.038 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.69 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.999 ? 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
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33780581]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257257]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893531]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39104562]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO58360	Lantana camara L.	Genus	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1859	Lantana camara	Species	Verbenaceae	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

Activity Type	# Activity
IC50	6
Inhibition	1

Activity Type	# Activity
Cell line	4
Unchecked	1
Protein complex group	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29671	Protein complex group	Nuclear factor NF-kappa-B complex	Homo sapiens	IC50	>	10000.0	nM	PMID[25027934]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[25027934]
NPT81	Cell line	A549	Homo sapiens	IC50	=	44.2	ug.mL-1	PMID[18553923]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	41.2	ug.mL-1	PMID[18553923]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	43.6	ug.mL-1	PMID[18553923]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	80.0	%	PMID[18553923]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	37.6	ug.mL-1	PMID[18553923]

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 NPC600880 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	23181
0.1-0.2	22994
0.2-0.3	2902
0.3-0.4	607
0.4-0.5	148
0.5-0.6	17
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC93744
0.8571	High Similarity	NPC476888
0.7273	Intermediate Similarity	NPC476890
0.7273	Intermediate Similarity	NPC476889
0.6795	Remote Similarity	NPC40918
0.6375	Remote Similarity	NPC603645
0.6234	Remote Similarity	NPC488521
0.6164	Remote Similarity	NPC267691
0.5952	Remote Similarity	NPC473576
0.5946	Remote Similarity	NPC274050
0.5946	Remote Similarity	NPC162632
0.5926	Remote Similarity	NPC23241
0.5921	Remote Similarity	NPC158141
0.5789	Remote Similarity	NPC263272
0.5714	Remote Similarity	NPC38754
0.5641	Remote Similarity	NPC120840
0.5517	Remote Similarity	NPC473483
0.5517	Remote Similarity	NPC475570
0.525	Remote Similarity	NPC173089
0.525	Remote Similarity	NPC200752
0.5244	Remote Similarity	NPC296164
0.519	Remote Similarity	NPC474845
0.5185	Remote Similarity	NPC193750
0.5065	Remote Similarity	NPC267517
0.5062	Remote Similarity	NPC291028

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC600880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6296
0.1-0.2	2809
0.2-0.3	39
0.3-0.4	5
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