NPASS Compound

Natural Product: NPC307097

Natural Product ID	NPC307097
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CGQPDIYJWNSEQF-BJNUSKFXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	70697751
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 94100 0 0 0 0 0 0 0 0999 V2000 9.1504 -0.2204 0.8615 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7413 1.2192 1.0275 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5678 1.4027 1.9492 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4171 2.0629 1.1787 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1463 1.1091 0.0068 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9478 1.5676 -0.8082 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3884 2.3326 -2.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3096 0.2296 -1.1809 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6779 -0.5809 0.0712 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4463 -0.2449 0.9391 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4096 -0.5479 -0.0552 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9948 -0.2319 0.2127 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4864 -0.8976 1.4992 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9150 -0.4574 1.6583 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 -0.2623 0.6388 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0974 0.1794 0.8551 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0677 -0.6917 0.1156 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5742 -1.2312 -1.1961 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1452 -1.6175 -1.2458 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2417 -0.4670 -0.7456 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6397 0.7214 -1.6071 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1941 -0.8416 -0.9161 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7372 -0.5889 -2.2742 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2006 -0.4049 -2.4068 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8244 0.3114 -1.2329 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2769 1.6964 -1.1837 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2910 -0.0771 -0.0438 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3385 -0.6794 0.5924 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9068 0.2523 1.6158 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0992 -0.2955 2.3545 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0423 -0.8872 1.3664 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3646 -1.7807 0.3582 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3542 -2.4098 -0.5861 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9038 -1.5260 -1.4888 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2901 -1.2058 -0.2608 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0270 -1.5943 2.0833 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7379 0.7918 2.9740 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9727 0.6161 2.5843 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8432 -0.1056 0.5535 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8969 -0.2755 -2.3148 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2344 1.1082 -0.8459 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3503 1.7448 -0.3391 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5105 -0.7275 0.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1880 -0.1982 0.4262 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2420 -0.7634 1.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6374 1.8141 1.3396 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8067 1.9571 2.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2043 0.3885 2.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5281 1.9889 1.8433 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6509 3.0739 0.8575 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3184 2.1605 -0.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1069 3.3991 -1.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9962 1.8165 -2.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5056 2.3073 -2.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6366 -1.6567 -0.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4940 0.7949 1.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4894 -0.9346 1.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4836 -1.6244 -0.3297 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7292 0.8198 0.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4984 -1.9859 1.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1252 -0.6109 2.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2780 -0.2985 2.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3552 0.0943 1.9540 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2273 1.2703 0.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2530 -1.5885 0.7697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7985 -0.5770 -2.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1719 -2.1706 -1.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8615 -1.8003 -2.2876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9763 -2.4947 -0.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6996 0.9555 -1.2886 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7405 0.4334 -2.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0810 1.6327 -1.3937 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2456 -1.9582 -0.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2731 0.3218 -2.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4387 -1.4310 -2.9356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4667 0.1824 -3.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7311 -1.3794 -2.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2742 2.1700 -0.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2874 1.7278 -1.6827 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9386 2.3354 -1.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9408 -1.5685 1.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2496 1.2225 1.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8147 -0.9928 3.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5861 -0.0808 0.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9474 -2.6435 0.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1851 -2.8128 0.0653 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9262 -3.3289 -1.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6397 -1.9848 -1.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3727 -0.9657 2.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1599 1.3356 2.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3848 1.3677 2.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8061 -1.2593 -2.3987 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2988 2.8368 -0.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2005 1.4716 -1.0310 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 6 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 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 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 9 39 1 0 8 40 1 6 5 41 1 6 41 42 1 0 42 2 1 0 39 5 1 0 25 8 1 0 35 28 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 6 51 1 1 7 52 1 0 7 53 1 0 7 54 1 0 9 55 1 6 10 56 1 0 10 57 1 0 11 58 1 6 12 59 1 1 13 60 1 0 13 61 1 0 14 62 1 0 16 63 1 0 16 64 1 0 17 65 1 1 18 66 1 0 18 67 1 0 19 68 1 0 19 69 1 0 21 70 1 0 21 71 1 0 21 72 1 0 22 73 1 1 23 74 1 0 23 75 1 0 24 76 1 0 24 77 1 0 26 78 1 0 26 79 1 0 26 80 1 0 28 81 1 1 29 82 1 6 30 83 1 1 31 84 1 6 32 85 1 1 33 86 1 0 33 87 1 0 34 88 1 0 36 89 1 0 37 90 1 0 38 91 1 0 40 92 1 0 42 93 1 0 42 94 1 0 M END

Standard InCHIKey	CGQPDIYJWNSEQF-BJNUSKFXSA-N
Standard InCHI	InChI=1S/C33H52O9/c1-17-7-12-32(39-16-17)18(2)33(38)25(42-32)14-23-21-6-5-19-13-20(8-10-30(19,3)22(21)9-11-31(23,33)4)40-29-28(37)27(36)26(35)24(15-34)41-29/h5,17-18,20-29,34-38H,6-16H2,1-4H3/t17-,18-,20+,21-,22+,23+,24-,25+,26-,27+,28-,29-,30+,31+,32-,33-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)[C@]3([C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)O)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	592.36	Volume:	595.904 ? Van der Waals volume.
Dense:	0.994	LogP:	3.089 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.428 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.449 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	138.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.313	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.878	Fsp³:	0.939
MCE-18:	175.375 ? 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:	0.847	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.181	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.046	MDCK Permeability:	-5.155
Pgp-inhibitor:	0.002	Pgp-substrate:	0.176
PAMPA:	0.905 ? 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%):	0.008	30% Bioavailability (F30%):	0.261
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166	MRP1:	0.009
Plasma Protein Binding (PPB):	69.696%	Volume Distribution (VD):	-0.446
Fu:	28.379% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.958
BSEP inhibitor:	0.663

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.019	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.969	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.335
HLM stability:	0.067 ? 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):

3.337

Half-life (T1/2):

2.518

ADMET: Toxicity

hERG Blockers:	0.09	hERG Blockers (10um):	0.273
Human Hepatotoxicity (H-HT):	0.543	Drug-induced Liver Injury (DILI):	0.937
AMES Toxicity:	0.83	Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.381	Skin Sensitization:	1.0
Carcinogencity:	0.474	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.058
Drug-induced Neurotoxicity:	0.027	Ototoxicity:	0.966
Hematotoxicity:	0.177	Drug-induced Nephrotoxicity:	0.61
Genotoxicity:	0.292	RPMI-8226 Immunitoxicity:	0.253
A549 Cytotoxicity:	0.782	Hek293 Cytotoxicity:	0.803
BCF:	1.743 ? 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:	3.462 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.62 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.083 ? 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
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	n.a.	stem	n.a.	PMID[18481024]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	stems	Yaound, village of Bangoua, near Bangangt	2007-APR	PMID[20553003]
NPO22180	Dracaena mannii	Species	Asparagaceae	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 NPC307097 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	21597
0.1-0.2	24013
0.2-0.3	3501
0.3-0.4	576
0.4-0.5	113
0.5-0.6	48
0.6-0.7	5
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
0.8295	Intermediate Similarity	NPC42482
0.8295	Intermediate Similarity	NPC40440
0.7634	Intermediate Similarity	NPC124677
0.7011	Intermediate Similarity	NPC181845
0.6522	Remote Similarity	NPC474399
0.6509	Remote Similarity	NPC167183
0.6344	Remote Similarity	NPC86020
0.62	Remote Similarity	NPC469347
0.6106	Remote Similarity	NPC32707
0.598	Remote Similarity	NPC469348
0.598	Remote Similarity	NPC477809
0.5922	Remote Similarity	NPC300557
0.59	Remote Similarity	NPC113044
0.59	Remote Similarity	NPC283829
0.59	Remote Similarity	NPC14704
0.59	Remote Similarity	NPC161676
0.5859	Remote Similarity	NPC470432
0.5859	Remote Similarity	NPC230507
0.5747	Remote Similarity	NPC158088
0.5728	Remote Similarity	NPC602423
0.5714	Remote Similarity	NPC480555
0.5714	Remote Similarity	NPC150372
0.5701	Remote Similarity	NPC486386
0.5596	Remote Similarity	NPC254255
0.5586	Remote Similarity	NPC477811
0.5568	Remote Similarity	NPC22140
0.5568	Remote Similarity	NPC243728
0.5566	Remote Similarity	NPC156789
0.5481	Remote Similarity	NPC197231
0.5472	Remote Similarity	NPC6806
0.5444	Remote Similarity	NPC282669
0.5429	Remote Similarity	NPC470433
0.5429	Remote Similarity	NPC46190
0.5429	Remote Similarity	NPC171073
0.5364	Remote Similarity	NPC309278
0.5327	Remote Similarity	NPC274200
0.531	Remote Similarity	NPC480553
0.5273	Remote Similarity	NPC475550
0.5268	Remote Similarity	NPC160084
0.5268	Remote Similarity	NPC473474
0.5263	Remote Similarity	NPC242748
0.5225	Remote Similarity	NPC13193
0.5185	Remote Similarity	NPC249553
0.5185	Remote Similarity	NPC182900
0.5179	Remote Similarity	NPC194207
0.5179	Remote Similarity	NPC22779
0.5135	Remote Similarity	NPC269297
0.5135	Remote Similarity	NPC222202
0.5133	Remote Similarity	NPC480554
0.5126	Remote Similarity	NPC477808
0.5096	Remote Similarity	NPC306991
0.5094	Remote Similarity	NPC19888
0.5089	Remote Similarity	NPC475333
0.5089	Remote Similarity	NPC224098
0.5089	Remote Similarity	NPC208383
0.5052	Remote Similarity	NPC296686
0.5051	Remote Similarity	NPC272015

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC307097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7307
0.1-0.2	1721
0.2-0.3	109
0.3-0.4	9
0.4-0.5	4
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