NPASS Compound

Natural Product: NPC259144

Natural Product ID	NPC259144
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SYDMVWLQJZBPIU-VHLOTGQHSA-N
IUPAC Name	n.a.
Synonyms	19-Hydroxybaccatin III
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL447792
PubChem CID	5318151
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 81 85 0 0 0 0 0 0 0 0999 V2000 -2.7603 0.1208 2.9549 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5389 0.3841 2.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7784 0.6817 0.8277 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6600 1.9269 0.8738 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4842 2.6463 2.0713 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3506 2.8874 -0.2312 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9514 3.3722 -0.1589 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0379 2.2439 -0.0738 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5760 0.8664 -0.0248 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5157 -0.1308 0.0859 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7951 0.5259 0.1689 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.4261 1.2399 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2308 -0.3039 2.2087 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9465 1.0782 1.3368 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4469 1.8523 0.3244 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6932 2.4781 0.4262 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4509 2.3168 1.5792 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9546 1.5377 2.6061 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7038 0.9239 2.4752 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6692 -1.1962 -0.9380 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1239 -2.4792 -0.4952 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5318 -2.1548 -0.8272 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8665 -2.0397 -2.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2290 -2.2848 -2.5216 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7457 -1.6394 -3.0154 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3717 -0.9044 -2.3501 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3848 -0.8069 -3.9764 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7378 -1.8312 -0.0817 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6412 -0.3681 0.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6198 0.1632 -0.2498 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7735 -2.6115 1.0965 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8145 -3.4287 1.4694 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8206 -3.5156 0.7410 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7520 -4.2018 2.7205 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3806 -3.5959 -1.3802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1313 -2.8384 0.9024 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9870 -1.6585 -0.8368 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6183 2.8714 1.0804 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4776 3.7708 1.1035 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8510 2.3119 -1.2351 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5951 3.3673 -1.6527 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6114 4.4212 -1.0137 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3963 3.2138 -2.9135 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5326 -0.2496 3.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8773 -0.4055 2.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1950 1.3046 2.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7417 1.7037 0.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2687 2.6533 2.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5324 2.4980 -1.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0293 3.7560 -0.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7715 4.1361 -0.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9709 0.7483 -1.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4660 -0.7036 1.0693 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8645 1.9773 -0.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0931 3.0891 -0.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4146 2.8039 1.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5468 1.4095 3.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3212 0.3208 3.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6682 -3.2554 -2.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1756 -2.4654 -3.6462 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9349 -1.4324 -2.4676 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4127 -2.5145 -3.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2342 0.1688 -2.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2717 -1.1660 -3.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8095 -0.7779 -4.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6834 -2.0418 -0.5668 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7104 -4.6861 2.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4703 -3.5793 3.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9457 -4.9786 2.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4384 -4.1415 -1.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8724 -4.4076 -0.7584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2005 -3.2731 -2.0600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5681 -2.5251 1.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2012 -2.6047 1.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1188 -3.9768 0.9633 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6203 -1.1148 -1.3578 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5690 3.4406 0.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6784 2.3746 2.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4574 3.4929 -2.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0077 3.8600 -3.7264 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3843 2.1635 -3.2690 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 4 5 1 0 4 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 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 10 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 22 28 1 0 28 29 1 0 29 30 2 0 28 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 21 35 1 0 21 36 1 0 20 37 1 6 8 38 1 0 38 39 1 0 8 40 1 6 40 41 1 0 41 42 2 0 41 43 1 0 29 3 1 0 9 3 1 0 19 14 1 0 26 20 1 0 39 7 1 0 1 44 1 0 2 45 1 0 2 46 1 0 4 47 1 6 5 48 1 0 6 49 1 0 6 50 1 0 7 51 1 6 9 52 1 6 10 53 1 1 15 54 1 0 16 55 1 0 17 56 1 0 18 57 1 0 19 58 1 0 24 59 1 0 24 60 1 0 24 61 1 0 25 62 1 6 26 63 1 0 26 64 1 0 27 65 1 0 28 66 1 6 34 67 1 0 34 68 1 0 34 69 1 0 35 70 1 0 35 71 1 0 35 72 1 0 36 73 1 0 36 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 38 78 1 0 43 79 1 0 43 80 1 0 43 81 1 0 M END

Standard InCHIKey	SYDMVWLQJZBPIU-VHLOTGQHSA-N
Standard InCHI	InChI=1S/C31H38O12/c1-15-19(35)12-31(39)26(42-27(38)18-9-7-6-8-10-18)24-29(13-32,20(36)11-21-30(24,14-40-21)43-17(3)34)25(37)23(41-16(2)33)22(15)28(31,4)5/h6-10,19-21,23-24,26,32,35-36,39H,11-14H2,1-5H3/t19-,20-,21+,23+,24-,26-,29+,30-,31+/m0/s1
SMILES	OC[C@]12[C@@H](O)C[C@@H]3[C@]([C@H]2[C@H](OC(=O)c2ccccc2)[C@]2(C(C(=C(C)[C@H](C2)O)[C@H](C1=O)OC(=O)C)(C)C)O)(CO3)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.24	Volume:	586.341 ? Van der Waals volume.
Dense:	1.027	LogP:	1.456 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.88 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.495 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	186.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.21	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.66	Fsp³:	0.613
MCE-18:	140.8 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.5	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.02 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.053	Promiscuous compounds:	0.476

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.883	MDCK Permeability:	-5.186
Pgp-inhibitor:	0.075	Pgp-substrate:	0.999
PAMPA:	0.995 ? 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):	0.002
20% Bioavailability (F20%):	0.983	30% Bioavailability (F30%):	0.983
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076	MRP1:	0.999
Plasma Protein Binding (PPB):	80.419%	Volume Distribution (VD):	-0.028
Fu:	20.297% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.003
BSEP inhibitor:	0.158

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.113	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.986
HLM stability:	0.316 ? 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):

5.849

Half-life (T1/2):

1.868

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.466	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.912	Skin Sensitization:	1.0
Carcinogencity:	0.936	Eye Corrosion:	0.0
Eye Irritation:	0.048	Respiratory Toxicity:	0.277
Drug-induced Neurotoxicity:	0.988	Ototoxicity:	0.636
Hematotoxicity:	0.963	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.756
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.918
BCF:	0.388 ? 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:	3.159 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.865 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.793 ? 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
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11554	Taxus sumatrana	Species	Taxaceae	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
Activity	1
Inhibition	4

Activity Type	# Activity
Cell line	5

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	Activity	=	2.2	ug ml-1	DrugMatrix in vivo data: Biochemistry
NPT376	Cell line	A498	Homo sapiens	Inhibition	=	26.7	%	PMID[16472241]
NPT405	Cell line	NCI-H226	Homo sapiens	Inhibition	=	44.6	%	PMID[16472241]
NPT81	Cell line	A549	Homo sapiens	Inhibition	=	0.0	%	PMID[16472241]
NPT306	Cell line	PC-3	Homo sapiens	Inhibition	=	47.7	%	PMID[19289528]

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 NPC259144 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	9353
0.1-0.2	37445
0.2-0.3	2574
0.3-0.4	417
0.4-0.5	29
0.5-0.6	29
0.6-0.7	7
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8442	Intermediate Similarity	NPC155329
0.8442	Intermediate Similarity	NPC114357
0.8228	Intermediate Similarity	NPC219419
0.775	Intermediate Similarity	NPC11588
0.6867	Remote Similarity	NPC197037
0.6867	Remote Similarity	NPC229545
0.6867	Remote Similarity	NPC134685
0.663	Remote Similarity	NPC471493
0.6207	Remote Similarity	NPC217918
0.6064	Remote Similarity	NPC603140
0.6023	Remote Similarity	NPC605573
0.5977	Remote Similarity	NPC38696
0.5743	Remote Similarity	NPC36607
0.573	Remote Similarity	NPC91730
0.573	Remote Similarity	NPC248265
0.573	Remote Similarity	NPC609501
0.5631	Remote Similarity	NPC471623
0.5631	Remote Similarity	NPC208553
0.5631	Remote Similarity	NPC181964
0.5631	Remote Similarity	NPC307628
0.5577	Remote Similarity	NPC33372
0.5577	Remote Similarity	NPC67246
0.5577	Remote Similarity	NPC324251
0.5577	Remote Similarity	NPC206211
0.5524	Remote Similarity	NPC487360
0.5524	Remote Similarity	NPC479182
0.5524	Remote Similarity	NPC479180
0.5524	Remote Similarity	NPC471629
0.5524	Remote Similarity	NPC306001
0.5481	Remote Similarity	NPC473400
0.5481	Remote Similarity	NPC603171
0.5421	Remote Similarity	NPC275170
0.5385	Remote Similarity	NPC92867
0.537	Remote Similarity	NPC486061
0.537	Remote Similarity	NPC486060
0.5321	Remote Similarity	NPC487361
0.5138	Remote Similarity	NPC471606
0.5094	Remote Similarity	NPC327699
0.5094	Remote Similarity	NPC473490
0.5054	Remote Similarity	NPC125882

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC259144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3117
0.1-0.2	5882
0.2-0.3	138
0.3-0.4	2
0.4-0.5	7
0.5-0.6	3
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
0.5631	Remote Similarity	NPD8485	Phase 4
0.5283	Remote Similarity	NPD8368	Phase 2
0.5094	Remote Similarity	NPD8424	Phase 3

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