NPASS Compound

Natural Product: NPC305902

Natural Product ID	NPC305902
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FNZPZCTVRVPPAB-YZSQHPIKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318183
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 76 80 0 0 0 0 0 0 0 0999 V2000 -3.2271 -3.3287 -1.9540 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1580 -2.8464 -1.0779 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4347 -1.9566 -0.1644 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4966 -1.0752 -0.6483 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7556 0.1141 -1.2271 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0917 0.1015 -2.4007 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8333 1.2105 -0.9003 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7075 2.1187 -0.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5806 1.9014 -2.2722 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3949 2.6624 -2.5184 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6889 2.7854 -1.4830 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2188 2.3128 -0.1264 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4546 3.5971 -0.2688 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6850 4.0756 -0.9950 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4901 0.9556 -0.3873 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0447 0.0331 0.6240 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2732 -1.4737 0.5356 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0864 -2.0930 -0.7582 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7210 -3.2946 -1.1900 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4624 -3.4932 -2.5647 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4388 -2.5225 -0.7697 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6326 -1.9098 1.0738 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1546 -0.9914 2.1355 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6190 -3.2693 1.6872 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6026 -2.0485 1.4739 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4094 -0.0419 0.4460 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2923 -0.0701 1.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8274 -0.0377 2.6551 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7170 -0.1377 1.2072 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1518 -0.1584 -0.0880 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5090 -0.2279 -0.4143 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4518 -0.2779 0.5837 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0255 -0.2577 1.9077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6761 -0.1885 2.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0930 2.2877 0.9095 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7760 3.2505 1.5270 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6283 4.4010 1.1358 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7258 3.0597 2.6774 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8066 2.4651 -2.6245 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2714 -0.7192 0.4501 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1748 -3.5612 -1.4246 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8791 -4.3074 -2.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3864 -2.7036 -2.8574 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2028 -1.5243 -1.3329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3135 2.8257 -0.5923 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2116 2.4754 0.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5387 1.4992 0.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5239 1.0138 -2.9959 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1842 2.3246 -3.4407 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7126 3.6957 -2.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6828 2.3971 -1.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2587 3.8464 -0.9194 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6132 4.2183 0.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0800 0.5953 -1.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2613 0.2622 1.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0327 -1.3988 -1.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4979 -4.2279 -0.7054 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5668 -2.5922 -2.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5856 -2.9452 -1.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5627 -1.1873 3.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1816 -1.3857 2.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2696 0.0470 1.8934 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4172 -3.9183 1.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9172 -3.2864 2.7778 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7083 -3.8481 1.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2238 -2.2120 2.3456 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4534 -0.1212 -0.9274 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8255 -0.2428 -1.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4914 -0.3311 0.2962 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7917 -0.2983 2.6641 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3967 -0.1756 3.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9762 4.0573 3.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6052 2.4762 2.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1452 2.5442 3.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8297 2.5480 -3.5991 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8406 -1.4714 0.6634 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 17 22 1 0 22 23 1 0 22 24 1 0 17 25 1 1 16 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 12 35 1 1 35 36 1 0 36 37 2 0 36 38 1 0 9 39 1 0 4 40 1 0 19 2 1 0 34 29 1 0 22 3 1 0 15 7 1 0 14 11 1 0 1 41 1 0 1 42 1 0 1 43 1 0 4 44 1 6 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 6 10 49 1 0 10 50 1 0 11 51 1 6 13 52 1 0 13 53 1 0 15 54 1 6 16 55 1 1 18 56 1 6 19 57 1 1 20 58 1 0 21 59 1 0 23 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 30 67 1 0 31 68 1 0 32 69 1 0 33 70 1 0 34 71 1 0 38 72 1 0 38 73 1 0 38 74 1 0 39 75 1 0 40 76 1 0 M END

Standard InCHIKey	FNZPZCTVRVPPAB-YZSQHPIKSA-N
Standard InCHI	InChI=1S/C29H36O11/c1-13-18-20(33)22(34)27(5)16(31)11-17-28(12-38-17,40-14(2)30)21(27)24(39-25(36)15-9-7-6-8-10-15)29(37,26(18,3)4)23(35)19(13)32/h6-10,16-17,19-21,23-24,31-33,35,37H,11-12H2,1-5H3/t16-,17+,19+,20+,21-,23-,24-,27+,28-,29+/m0/s1
SMILES	CC1=C2[C@H](C(=O)[C@]3(C)[C@H](C[C@@H]4[C@@](CO4)([C@H]3[C@@H]([C@]([C@H]([C@@H]1O)O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	560.23	Volume:	545.595 ? Van der Waals volume.
Dense:	1.027	LogP:	1.388 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.821 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.219 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	29.0
TPSA:	180.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.249	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.704	Fsp³:	0.621
MCE-18:	142.128 ? 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:	0.581	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.055	Promiscuous compounds:	0.254

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.615	MDCK Permeability:	-4.857
Pgp-inhibitor:	0.217	Pgp-substrate:	1.0
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):	0.001
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.998
Plasma Protein Binding (PPB):	73.205%	Volume Distribution (VD):	-0.287
Fu:	24.681% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.973	BCRP inhibitor:	0.012
BSEP inhibitor:	0.661

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:	0.017	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.534
HLM stability:	0.757 ? 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):

4.018

Half-life (T1/2):

3.163

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.108
Human Hepatotoxicity (H-HT):	0.562	Drug-induced Liver Injury (DILI):	0.857
AMES Toxicity:	0.842	Rat Oral Acute Toxicity:	0.718
Maximum Recommended Daily Dose:	0.381	Skin Sensitization:	0.998
Carcinogencity:	0.268	Eye Corrosion:	0.0
Eye Irritation:	0.134	Respiratory Toxicity:	0.698
Drug-induced Neurotoxicity:	0.216	Ototoxicity:	0.752
Hematotoxicity:	0.909	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.261
A549 Cytotoxicity:	0.695	Hek293 Cytotoxicity:	0.263
BCF:	0.39 ? 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:	3.091 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.716 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.812 ? 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
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
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]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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]
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]

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 NPC305902 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	8212
0.1-0.2	38422
0.2-0.3	2735
0.3-0.4	417
0.4-0.5	27
0.5-0.6	35
0.6-0.7	6
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
0.7763	Intermediate Similarity	NPC229545
0.7763	Intermediate Similarity	NPC134685
0.7308	Intermediate Similarity	NPC248265
0.6506	Remote Similarity	NPC11588
0.631	Remote Similarity	NPC155329
0.631	Remote Similarity	NPC114357
0.6265	Remote Similarity	NPC197037
0.6082	Remote Similarity	NPC453583
0.6071	Remote Similarity	NPC91730
0.5979	Remote Similarity	NPC321072
0.5979	Remote Similarity	NPC215892
0.5979	Remote Similarity	NPC242662
0.5979	Remote Similarity	NPC102167
0.5979	Remote Similarity	NPC488127
0.5882	Remote Similarity	NPC609501
0.5876	Remote Similarity	NPC473300
0.5859	Remote Similarity	NPC471754
0.5859	Remote Similarity	NPC479183
0.5859	Remote Similarity	NPC479181
0.5758	Remote Similarity	NPC317882
0.5632	Remote Similarity	NPC605573
0.5618	Remote Similarity	NPC259144
0.5532	Remote Similarity	NPC603140
0.5455	Remote Similarity	NPC217918
0.5392	Remote Similarity	NPC33372
0.5392	Remote Similarity	NPC67246
0.5341	Remote Similarity	NPC92867
0.534	Remote Similarity	NPC478329
0.5275	Remote Similarity	NPC219419
0.5227	Remote Similarity	NPC38696
0.5146	Remote Similarity	NPC471623
0.5146	Remote Similarity	NPC208553
0.5146	Remote Similarity	NPC181964
0.5146	Remote Similarity	NPC307628
0.5146	Remote Similarity	NPC191193
0.5098	Remote Similarity	NPC36607
0.5096	Remote Similarity	NPC324251
0.5096	Remote Similarity	NPC206211
0.5056	Remote Similarity	NPC132599
0.5048	Remote Similarity	NPC487360
0.5048	Remote Similarity	NPC479182
0.5048	Remote Similarity	NPC479180
0.5048	Remote Similarity	NPC471629
0.5048	Remote Similarity	NPC306001

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3024
0.1-0.2	5929
0.2-0.3	184
0.3-0.4	2
0.4-0.5	8
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
0.5979	Remote Similarity	NPD8360	Approved
0.5979	Remote Similarity	NPD8361	Phase 4
0.5146	Remote Similarity	NPD8485	Phase 4

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