NPASS Compound

Natural Product: NPC268320

Natural Product ID	NPC268320
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	APFPLZLTXJYXMM-MTLPDSHASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	643707
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 98103 0 0 0 0 0 0 0 0999 V2000 -8.2827 -0.2013 -0.7697 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9787 0.4988 -0.4956 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6991 1.4979 -1.6046 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9854 1.2757 0.7894 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4066 0.5336 1.9430 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9909 0.0432 1.6887 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9953 0.9842 2.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5869 0.6062 2.0894 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2370 0.1608 0.7055 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8781 1.4223 -0.0996 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3645 -0.4362 -0.0478 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1758 -1.3421 -0.9655 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8436 -1.8924 -1.3860 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7451 -1.0799 -0.7276 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6425 -1.5597 -1.0245 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9053 -2.9992 -0.7610 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7956 -1.3608 -2.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1668 -1.5954 -3.0362 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2782 -1.2972 -2.1263 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9915 -0.5475 -0.8611 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8486 -1.1292 0.2160 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3520 0.9027 -1.0805 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5662 1.2986 -1.4337 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8379 1.3722 -0.9116 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9047 0.9585 0.2675 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9223 1.8854 -1.7118 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1483 1.9482 -1.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7288 1.4972 -0.1527 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4404 0.4309 0.6158 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0265 0.2248 1.8508 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9452 1.1288 2.3312 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2824 2.2451 1.5765 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6845 2.4137 0.3704 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5649 0.9783 3.5576 O 0 0 0 0 0 1 0 0 0 0 0 0 1.5681 -0.6013 -0.3800 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4237 -0.6924 1.1224 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0326 -0.2270 1.4822 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0762 -0.8272 0.7066 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5201 -2.0957 1.4118 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1105 -2.4270 -1.9146 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7072 0.0813 0.2183 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8335 -0.5299 -0.5376 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8827 -1.2999 2.2872 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0827 -1.5089 3.2584 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6032 -2.4075 1.8735 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0915 0.1293 -0.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1480 -1.2971 -0.5831 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5742 -0.1112 -1.8401 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8181 1.2132 -2.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5022 2.5153 -1.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5492 1.5756 -2.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0564 1.4797 1.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4860 2.2816 0.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3656 1.1929 2.8127 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0636 -0.3256 2.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1930 0.9593 3.4204 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2176 2.0108 1.9453 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2692 -0.0914 2.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9601 1.5270 2.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4739 2.2460 0.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2651 1.3598 -1.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.6947 -0.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0187 -1.7637 -1.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7787 -2.9630 -1.1484 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8159 -1.7813 -2.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8129 -0.0669 -1.2355 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3713 -3.2462 0.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6078 -3.4114 -1.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0302 -3.6742 -0.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4840 -0.3372 -2.7660 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0820 -2.0467 -3.0815 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2304 -1.0740 -4.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2288 -2.6842 -3.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9927 -0.6460 -2.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3748 -2.0640 0.6545 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9477 -0.4743 1.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8581 -1.4066 -0.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6282 1.3245 -1.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0379 1.4994 -0.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6693 2.2730 -2.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8956 2.3976 -2.1349 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7849 -0.3462 0.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7562 -0.6420 2.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0197 2.9660 1.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9609 3.2929 -0.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1154 0.4173 -0.6076 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5266 -1.7173 1.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1122 0.0224 1.6395 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -0.5216 2.5759 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0588 0.8881 1.5094 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5052 -1.9253 2.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7513 -2.9137 1.2668 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5232 -2.4372 1.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9056 -2.9189 -1.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7055 1.2184 -0.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6403 -0.6339 -1.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2083 -1.4639 -0.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2232 -3.3456 1.8671 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 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 31 34 1 0 20 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 1 19 40 1 0 11 41 1 0 41 42 1 0 6 43 1 1 43 44 2 0 43 45 1 0 42 2 1 0 41 6 1 0 38 9 1 0 38 14 1 0 35 15 1 0 33 28 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 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 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 10 60 1 0 10 61 1 0 10 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 14 66 1 6 16 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 18 73 1 0 19 74 1 6 21 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 26 80 1 0 27 81 1 0 29 82 1 0 30 83 1 0 32 84 1 0 33 85 1 0 35 86 1 6 36 87 1 0 36 88 1 0 37 89 1 0 37 90 1 0 39 91 1 0 39 92 1 0 39 93 1 0 40 94 1 0 41 95 1 6 42 96 1 0 42 97 1 0 45 98 1 0 M CHG 1 34 -1 M END

Standard InCHIKey	APFPLZLTXJYXMM-MTLPDSHASA-N
Standard InCHI	InChI=1S/C39H54O6/c1-34(2)19-21-39(33(43)44)22-20-37(5)27(28(39)23-34)12-13-30-35(3)17-16-31(41)36(4,29(35)15-18-38(30,37)6)24-45-32(42)14-9-25-7-10-26(40)11-8-25/h7-12,14,28-31,40-41H,13,15-24H2,1-6H3,(H,43,44)/p-1/b14-9-/t28-,29-,30-,31+,35+,36+,37-,38-,39+/m1/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(COC(=O)/C=Cc6ccc(cc6)[O-])[C@@H]5CC[C@@]34C)O)[C@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.39	Volume:	666.047 ? Van der Waals volume.
Dense:	0.928	LogP:	4.129 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.608 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.141 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	35.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.175	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.911	Fsp³:	0.692
MCE-18:	162.273 ? 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:	0.98	Fluc inhibitor:	0.932 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.033 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.036 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.155	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.622	MDCK Permeability:	-5.076
Pgp-inhibitor:	0.006	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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%):	0.722	30% Bioavailability (F30%):	0.053
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041	MRP1:	0.747
Plasma Protein Binding (PPB):	97.009%	Volume Distribution (VD):	-0.358
Fu:	2.29% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.524	BCRP inhibitor:	0.031
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.037	CYP2C19-substrate:	0.731
CYP2C9-inhibitor:	0.127	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.966 ? 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):

3.115

Half-life (T1/2):

1.17

ADMET: Toxicity

hERG Blockers:	0.128	hERG Blockers (10um):	0.146
Human Hepatotoxicity (H-HT):	0.701	Drug-induced Liver Injury (DILI):	0.289
AMES Toxicity:	0.239	Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.539	Skin Sensitization:	0.999
Carcinogencity:	0.381	Eye Corrosion:	0.0
Eye Irritation:	0.325	Respiratory Toxicity:	0.861
Drug-induced Neurotoxicity:	0.061	Ototoxicity:	0.515
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.865
Genotoxicity:	0.358	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.872	Hek293 Cytotoxicity:	0.615
BCF:	1.04 ? 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:	4.431 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.851 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.365 ? 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
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738395]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23148	Ludwigia octovalvis	Species	Onagraceae	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

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

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 NPC268320 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	9210
0.1-0.2	35735
0.2-0.3	4191
0.3-0.4	423
0.4-0.5	208
0.5-0.6	61
0.6-0.7	20
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8488	Intermediate Similarity	NPC198621
0.8488	Intermediate Similarity	NPC216940
0.6915	Remote Similarity	NPC262970
0.66	Remote Similarity	NPC206232
0.66	Remote Similarity	NPC14515
0.6489	Remote Similarity	NPC18982
0.6354	Remote Similarity	NPC171007
0.6354	Remote Similarity	NPC190849
0.6341	Remote Similarity	NPC480946
0.6341	Remote Similarity	NPC130577
0.6341	Remote Similarity	NPC142415
0.6341	Remote Similarity	NPC102683
0.6162	Remote Similarity	NPC605663
0.6122	Remote Similarity	NPC22676
0.6122	Remote Similarity	NPC488215
0.6118	Remote Similarity	NPC298554
0.6071	Remote Similarity	NPC270768
0.6071	Remote Similarity	NPC59263
0.6071	Remote Similarity	NPC210106
0.604	Remote Similarity	NPC479747
0.604	Remote Similarity	NPC479746
0.602	Remote Similarity	NPC271494
0.5955	Remote Similarity	NPC474727
0.5941	Remote Similarity	NPC132126
0.5905	Remote Similarity	NPC601567
0.5905	Remote Similarity	NPC606631
0.5882	Remote Similarity	NPC482049
0.5882	Remote Similarity	NPC482050
0.5865	Remote Similarity	NPC479740
0.5865	Remote Similarity	NPC479741
0.5842	Remote Similarity	NPC54627
0.5842	Remote Similarity	NPC249817
0.5825	Remote Similarity	NPC610795
0.5784	Remote Similarity	NPC606782
0.5741	Remote Similarity	NPC53520
0.5728	Remote Similarity	NPC475482
0.5714	Remote Similarity	NPC173569
0.5607	Remote Similarity	NPC310729
0.5607	Remote Similarity	NPC150310
0.5568	Remote Similarity	NPC200752
0.5517	Remote Similarity	NPC182797
0.5517	Remote Similarity	NPC52169
0.5517	Remote Similarity	NPC488562
0.5455	Remote Similarity	NPC158141
0.5446	Remote Similarity	NPC475627
0.5402	Remote Similarity	NPC198664
0.54	Remote Similarity	NPC43353
0.5385	Remote Similarity	NPC488214
0.5377	Remote Similarity	NPC473773
0.5377	Remote Similarity	NPC475311
0.5377	Remote Similarity	NPC475579
0.5341	Remote Similarity	NPC282616
0.5341	Remote Similarity	NPC275809
0.5341	Remote Similarity	NPC121798
0.5341	Remote Similarity	NPC64872
0.5341	Remote Similarity	NPC84319
0.5341	Remote Similarity	NPC25906
0.5341	Remote Similarity	NPC234346
0.5341	Remote Similarity	NPC52021
0.5341	Remote Similarity	NPC599947
0.5333	Remote Similarity	NPC474963
0.5281	Remote Similarity	NPC231063
0.5281	Remote Similarity	NPC282395
0.5281	Remote Similarity	NPC130278
0.5281	Remote Similarity	NPC481360
0.5281	Remote Similarity	NPC110308
0.5222	Remote Similarity	NPC228784
0.5222	Remote Similarity	NPC324341
0.5222	Remote Similarity	NPC120840
0.5222	Remote Similarity	NPC601810
0.5152	Remote Similarity	NPC283849
0.5152	Remote Similarity	NPC28198
0.5152	Remote Similarity	NPC476123
0.5149	Remote Similarity	NPC100383
0.5116	Remote Similarity	NPC604575
0.5111	Remote Similarity	NPC106112
0.5111	Remote Similarity	NPC261935
0.5094	Remote Similarity	NPC172311
0.5054	Remote Similarity	NPC222047
0.5049	Remote Similarity	NPC284807
0.5047	Remote Similarity	NPC304110
0.5047	Remote Similarity	NPC27518
0.5047	Remote Similarity	NPC611516

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC268320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3298
0.1-0.2	5767
0.2-0.3	81
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
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
0.5784	Remote Similarity	NPD8166	Discontinued

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