NPASS Compound

Natural Product: NPC600872

Natural Product ID	NPC600872
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LZUAWASJLVYVGM-KYJUHHDHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504018
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 95100 0 0 0 0 0 0 0 0999 V2000 9.0828 3.3698 -2.1913 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8914 2.2760 -1.3133 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5924 1.8632 -1.0256 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4788 2.4786 -1.5611 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1971 2.0708 -1.2766 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9656 1.0095 -0.4283 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5721 0.5743 -0.1353 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 1.2904 1.0167 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5828 0.8354 1.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.1406 0.4050 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4634 -0.2751 0.7113 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1717 -0.9632 -0.1985 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7422 -2.1805 -0.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7477 -3.0490 0.8522 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3368 -4.2957 0.8107 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3389 -5.1714 1.8951 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7092 -4.7642 3.0873 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9610 -4.7150 -0.3574 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5651 -5.9705 -0.4289 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2024 -6.4026 -1.6126 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9718 -3.8829 -1.4254 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3731 -2.6167 -1.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4357 -1.8051 -2.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5407 -0.8045 -2.6303 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5762 0.2114 -1.5884 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3351 0.1456 -0.4413 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3590 1.1656 0.4910 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1341 1.0942 1.6547 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6020 2.3126 0.2971 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6220 3.3413 1.2322 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8567 4.4932 1.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8427 2.3916 -0.8378 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8317 1.3594 -1.7621 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0331 1.4273 -3.0128 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8522 0.9566 -4.1553 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6595 -0.1967 -3.9617 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0529 0.0035 -4.2574 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9518 0.0527 1.9483 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2377 -0.3485 2.2743 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7448 -0.0119 3.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2017 0.7685 2.8784 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1001 1.1702 2.5429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8754 1.9395 3.5452 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 2.0033 3.2700 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6768 1.0600 2.2493 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7628 -0.2912 2.6764 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0614 0.3810 0.1169 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3391 0.8002 -0.1765 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4633 0.1628 0.3767 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1649 3.5343 -2.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5190 3.1383 -3.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6332 4.2939 -1.7761 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6884 3.3248 -2.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3868 2.6056 -1.7360 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5246 -0.5101 -0.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9698 0.8372 -1.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9319 2.3690 0.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2415 -0.1059 -0.5539 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2731 -2.8066 1.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8731 -5.5138 3.8938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6052 -4.6961 2.9111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0809 -3.7926 3.4647 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7050 -7.3841 -1.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4204 -6.6397 -2.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9841 -5.7312 -1.9762 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4644 -4.2073 -2.3553 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -2.5264 -3.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4383 -1.3442 -2.8463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4939 -1.4058 -2.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9381 -0.7359 -0.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8234 0.3473 1.7746 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7593 4.3126 1.2179 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0152 4.8847 0.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1902 5.2869 1.7658 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2476 3.2893 -0.9909 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0236 0.9838 -2.9165 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8167 2.5241 -3.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2218 0.8217 -5.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5595 1.7972 -4.4233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7320 -0.2451 -3.4116 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1788 1.0981 -4.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3645 -0.5268 -5.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8588 1.0868 3.6720 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0114 -0.3529 4.3052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6897 -0.5488 3.7786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5938 1.0264 3.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6613 1.5463 4.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4451 2.9842 3.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9747 1.8082 4.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6354 3.0215 2.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4602 -1.0214 1.8998 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9930 -0.4176 3.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7233 -0.5462 3.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9254 -0.4637 0.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6819 -0.8044 0.1318 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 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 15 18 2 0 18 19 1 0 19 20 1 0 18 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 27 29 2 0 29 30 1 0 30 31 1 0 29 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 11 38 2 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 2 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 6 47 1 0 47 48 2 0 48 49 1 0 48 3 1 0 45 8 1 0 42 9 1 0 22 13 1 0 36 24 1 0 33 25 1 0 1 50 1 0 1 51 1 0 1 52 1 0 4 53 1 0 5 54 1 0 7 55 1 0 7 56 1 0 8 57 1 6 10 58 1 0 14 59 1 0 17 60 1 0 17 61 1 0 17 62 1 0 20 63 1 0 20 64 1 0 20 65 1 0 21 66 1 0 23 67 1 0 23 68 1 0 24 69 1 1 26 70 1 0 28 71 1 0 31 72 1 0 31 73 1 0 31 74 1 0 32 75 1 0 34 76 1 0 34 77 1 0 35 78 1 0 35 79 1 0 37 80 1 0 37 81 1 0 37 82 1 0 40 83 1 0 40 84 1 0 40 85 1 0 41 86 1 0 43 87 1 0 43 88 1 0 44 89 1 0 44 90 1 0 46 91 1 0 46 92 1 0 46 93 1 0 47 94 1 0 49 95 1 0 M END

Standard InCHIKey	LZUAWASJLVYVGM-KYJUHHDHSA-N
Standard InCHI	InChI=1S/C39H46N2O8/c1-40-12-11-25-18-37(47-6)39(21-28(25)29(40)14-23-8-9-33(44-3)31(42)15-23)49-34-22-38(48-7)36(46-5)19-26(34)16-30-27-20-32(43)35(45-4)17-24(27)10-13-41(30)2/h8-9,15,17-22,29-30,42-43H,10-14,16H2,1-7H3/t29-,30-/m0/s1
SMILES	COc1ccc(C[C@H]2c3cc(Oc4cc(OC)c(OC)cc4C[C@H]4c5cc(O)c(OC)cc5CCN4C)c(OC)cc3CCN2C)cc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	670.33	Volume:	692.439 ? Van der Waals volume.
Dense:	0.968	LogP:	2.832 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.673 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.283 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	34.0
TPSA:	102.32 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.185	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.862	Fsp³:	0.385
MCE-18:	119.222 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.872	Fluc inhibitor:	0.152 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.908 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.814 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.214

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.093	MDCK Permeability:	-4.783
Pgp-inhibitor:	0.979	Pgp-substrate:	0.078
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):	0.0
20% Bioavailability (F20%):	0.818	30% Bioavailability (F30%):	0.252
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.991
Plasma Protein Binding (PPB):	61.536%	Volume Distribution (VD):	-0.106
Fu:	38.107% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.995
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.011
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.827
HLM stability:	0.213 ? 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):

5.377

Half-life (T1/2):

3.464

ADMET: Toxicity

hERG Blockers:	0.846	hERG Blockers (10um):	0.793
Human Hepatotoxicity (H-HT):	0.841	Drug-induced Liver Injury (DILI):	0.063
AMES Toxicity:	0.484	Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.989	Skin Sensitization:	0.685
Carcinogencity:	0.268	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.706
Drug-induced Neurotoxicity:	0.9	Ototoxicity:	0.888
Hematotoxicity:	0.061	Drug-induced Nephrotoxicity:	0.189
Genotoxicity:	0.552	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.334	Hek293 Cytotoxicity:	0.901
BCF:	1.712 ? 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:	4.247 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.074 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.022 ? 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
NPO14144	Hernandia peltata	Species	Hernandiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np960034d]
NPO14144	Hernandia peltata	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3987/R-1980-04-0397]
NPO14144	Hernandia peltata	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987061]
NPO14144	Hernandia peltata	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14144	Hernandia peltata	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18997	Hernandia sonora	Species	Hernandiaceae	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	2
Selectivity Index	2
ED50	1

Activity Type	# Activity
Cell line	1
Organism	2
Unchecked	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
NPT91	Cell line	KB	Homo sapiens	ED50	>	29900.0	nM	PMID[9917283]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	61.0	nM	PMID[9917283]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	164.0	nM	PMID[9917283]
NPT28438	Unchecked	Unchecked	n.a.	Selectivity Index	>	490.0	n.a.	PMID[9917283]
NPT28438	Unchecked	Unchecked	n.a.	Selectivity Index	>	180.0	n.a.	PMID[9917283]

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 NPC600872 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	27674
0.1-0.2	20342
0.2-0.3	1558
0.3-0.4	137
0.4-0.5	84
0.5-0.6	51
0.6-0.7	9
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	Natural Product ID
0.7015	Intermediate Similarity	NPC147390
0.7015	Intermediate Similarity	NPC428
0.6912	Remote Similarity	NPC135538
0.6912	Remote Similarity	NPC24233
0.6753	Remote Similarity	NPC603603
0.6456	Remote Similarity	NPC610959
0.6353	Remote Similarity	NPC601489
0.6353	Remote Similarity	NPC604804
0.6282	Remote Similarity	NPC480592
0.625	Remote Similarity	NPC240841
0.6145	Remote Similarity	NPC286119
0.5949	Remote Similarity	NPC256012
0.5949	Remote Similarity	NPC610965
0.5753	Remote Similarity	NPC321505
0.5753	Remote Similarity	NPC179825
0.5581	Remote Similarity	NPC311973
0.5581	Remote Similarity	NPC239824
0.5581	Remote Similarity	NPC600054
0.5581	Remote Similarity	NPC601504
0.5529	Remote Similarity	NPC290582
0.5529	Remote Similarity	NPC217748
0.5529	Remote Similarity	NPC182052
0.5529	Remote Similarity	NPC271013
0.5529	Remote Similarity	NPC42663
0.5529	Remote Similarity	NPC15414
0.5513	Remote Similarity	NPC152680
0.5465	Remote Similarity	NPC279228
0.5393	Remote Similarity	NPC181796
0.5393	Remote Similarity	NPC290005
0.5393	Remote Similarity	NPC54654
0.5393	Remote Similarity	NPC7715
0.5393	Remote Similarity	NPC328155
0.5393	Remote Similarity	NPC222661
0.5393	Remote Similarity	NPC285931
0.5375	Remote Similarity	NPC317272
0.5375	Remote Similarity	NPC268503
0.5341	Remote Similarity	NPC601503
0.5325	Remote Similarity	NPC247639
0.5325	Remote Similarity	NPC25084
0.5287	Remote Similarity	NPC606311
0.5211	Remote Similarity	NPC314682
0.52	Remote Similarity	NPC191376
0.5169	Remote Similarity	NPC185639
0.5169	Remote Similarity	NPC251735
0.5169	Remote Similarity	NPC254441
0.5169	Remote Similarity	NPC116465
0.5169	Remote Similarity	NPC49075
0.5169	Remote Similarity	NPC223690
0.5169	Remote Similarity	NPC9532
0.5169	Remote Similarity	NPC599951
0.5165	Remote Similarity	NPC47077
0.5139	Remote Similarity	NPC213206
0.5139	Remote Similarity	NPC188163
0.5139	Remote Similarity	NPC328750
0.5135	Remote Similarity	NPC185838
0.5109	Remote Similarity	NPC212237
0.5057	Remote Similarity	NPC480591
0.5054	Remote Similarity	NPC24260
0.5054	Remote Similarity	NPC275680
0.5054	Remote Similarity	NPC22115
0.5054	Remote Similarity	NPC605743
0.5054	Remote Similarity	NPC611658

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC600872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4460
0.1-0.2	4551
0.2-0.3	127
0.3-0.4	5
0.4-0.5	5
0.5-0.6	2
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
0.5256	Remote Similarity	NPD4010	Discontinued
0.5139	Remote Similarity	NPD4664	Clinical (unspecified phase)

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