NPASS Compound

Natural Product: NPC297498

Natural Product ID	NPC297498
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VCBRFHLMVHXWFV-RJNXOFJDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10493
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 83 88 0 0 0 0 0 0 0 0999 V2000 7.0302 2.0987 -1.9773 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3196 0.9641 -1.3128 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2288 -0.2581 -1.1609 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5158 -1.3428 -0.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2079 -1.6047 -1.1091 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4060 -0.3436 -1.2597 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1130 0.6509 -1.8647 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8512 0.1260 -0.1065 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5025 0.1752 -0.0325 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0781 -0.8195 1.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6014 -0.9941 0.9219 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0948 0.3019 1.2656 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0920 0.4539 2.7637 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6131 -0.3551 3.4654 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4553 1.4828 0.5834 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2499 1.9255 -0.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7382 1.9575 -0.5609 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2145 1.3959 0.7667 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 0.1048 1.1064 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0119 -0.9639 0.1743 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4684 -1.1928 0.3578 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3232 -0.0424 0.7388 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0513 -0.4457 2.0255 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3621 0.1520 -0.3167 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8136 1.5725 -0.1308 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4368 2.2512 -0.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6767 1.2827 0.8875 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0179 1.7791 2.1757 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4921 -0.8125 -0.2907 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7634 -0.5009 -0.1170 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5548 -1.7147 -0.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8284 -1.7623 -0.0193 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6936 -2.7626 -0.3633 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3935 -2.2646 -0.4536 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7308 -0.7969 -1.1526 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9448 1.5238 0.3759 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2743 -2.4867 -0.3163 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6039 -2.7941 1.0234 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3808 0.0838 -0.4554 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2893 2.8739 -2.2659 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7514 2.6154 -1.2985 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6404 1.7687 -2.8555 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1175 1.2881 -0.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5257 -0.5848 -2.1583 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3530 -0.9523 0.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5240 -1.9101 -2.1420 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6411 -2.4397 -0.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5518 -0.6067 -1.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9355 -0.1686 -0.9198 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6368 -1.7728 0.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3581 -0.4225 2.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2171 -1.7521 1.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4126 -1.3029 -0.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2783 1.3698 3.2265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2827 2.3473 1.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1087 2.9265 -0.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0406 1.2464 -1.4856 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2368 1.4397 -1.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1136 3.0031 -0.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8096 2.1481 1.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9836 -0.1928 2.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4404 -1.8977 0.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8295 -1.6454 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5700 -2.0635 1.0766 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1680 0.3963 2.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0011 -0.9725 1.8291 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3859 -1.1643 2.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8749 0.0813 -1.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4145 1.7461 0.7621 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3471 1.9467 -1.0080 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0463 2.2914 -1.0437 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5045 3.2544 0.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2865 1.6480 2.8077 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1146 0.5304 0.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7094 -2.7476 0.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0479 -2.5331 -1.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8469 -1.6588 -1.6075 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2808 2.3281 -0.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4068 1.7182 1.3888 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2129 -3.7097 1.0770 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1585 -1.8878 1.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6961 -2.9885 1.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1445 0.3823 0.4700 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 1 13 14 2 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 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 24 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 20 35 1 0 15 36 1 0 4 37 1 0 37 38 1 0 3 39 1 0 7 2 1 0 36 9 1 0 19 12 1 0 27 22 1 0 34 29 1 0 27 18 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 3 44 1 6 4 45 1 0 5 46 1 0 5 47 1 0 6 48 1 6 9 49 1 6 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 15 55 1 1 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 19 61 1 0 20 62 1 1 21 63 1 0 21 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 6 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 28 73 1 0 30 74 1 0 34 75 1 0 34 76 1 0 35 77 1 0 36 78 1 0 36 79 1 0 38 80 1 0 38 81 1 0 38 82 1 0 39 83 1 0 M END

Standard InCHIKey	VCBRFHLMVHXWFV-RJNXOFJDSA-N
Standard InCHI	InChI=1S/C30H44O9/c1-16-27(34)23(36-3)12-25(38-16)39-19-6-8-29(15-31)18(11-19)4-5-21-26(29)22(32)13-28(2)20(7-9-30(21,28)35)17-10-24(33)37-14-17/h10,15-16,18-23,25-27,32,34-35H,4-9,11-14H2,1-3H3/t16?,18-,19+,20-,21?,22-,23?,25-,26?,27-,28-,29-,30+/m1/s1
SMILES	CC1[C@H](C(C[C@H](O1)O[C@H]1CC[C@@]2(C=O)[C@H](CCC3C2[C@@H](C[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)O)C1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	548.3	Volume:	547.3 ? Van der Waals volume.
Dense:	1.002	LogP:	1.394 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.89 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.577 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	131.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.269	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.451	Fsp³:	0.867
MCE-18:	110.036 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.734	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.095	Promiscuous compounds:	0.08

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.238	MDCK Permeability:	-4.992
Pgp-inhibitor:	0.003	Pgp-substrate:	1.0
PAMPA:	0.999 ? 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):	0.017
20% Bioavailability (F20%):	0.884	30% Bioavailability (F30%):	0.827
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.874
Plasma Protein Binding (PPB):	56.388%	Volume Distribution (VD):	0.057
Fu:	43.557% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.792
OATP1B3 inhibitor:	0.45	BCRP inhibitor:	0.006
BSEP inhibitor:	0.957

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.405	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.0 ? 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):

5.465

Half-life (T1/2):

3.53

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.346
Human Hepatotoxicity (H-HT):	0.799	Drug-induced Liver Injury (DILI):	0.778
AMES Toxicity:	0.932	Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.995	Skin Sensitization:	1.0
Carcinogencity:	0.915	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.508
Drug-induced Neurotoxicity:	0.102	Ototoxicity:	0.956
Hematotoxicity:	0.403	Drug-induced Nephrotoxicity:	0.973
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.527
A549 Cytotoxicity:	0.157	Hek293 Cytotoxicity:	0.744
BCF:	0.507 ? 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:	3.303 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.104 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.123 ? 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
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9481	Strophanthus divaricatus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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 NPC297498 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	13042
0.1-0.2	33887
0.2-0.3	2629
0.3-0.4	88
0.4-0.5	149
0.5-0.6	47
0.6-0.7	10
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
0.7531	Intermediate Similarity	NPC84949
0.7531	Intermediate Similarity	NPC480562
0.7531	Intermediate Similarity	NPC74945
0.7531	Intermediate Similarity	NPC31354
0.7531	Intermediate Similarity	NPC69576
0.7349	Intermediate Similarity	NPC483822
0.6824	Remote Similarity	NPC180079
0.6588	Remote Similarity	NPC34390
0.6437	Remote Similarity	NPC250556
0.6395	Remote Similarity	NPC99080
0.6322	Remote Similarity	NPC152615
0.625	Remote Similarity	NPC484212
0.6042	Remote Similarity	NPC329986
0.6042	Remote Similarity	NPC140092
0.6023	Remote Similarity	NPC469750
0.6	Remote Similarity	NPC484202
0.5978	Remote Similarity	NPC103534
0.5978	Remote Similarity	NPC44899
0.5978	Remote Similarity	NPC304260
0.5978	Remote Similarity	NPC29639
0.58	Remote Similarity	NPC329636
0.5795	Remote Similarity	NPC471633
0.5778	Remote Similarity	NPC199428
0.5778	Remote Similarity	NPC109448
0.5778	Remote Similarity	NPC310341
0.5778	Remote Similarity	NPC480914
0.5652	Remote Similarity	NPC179412
0.5652	Remote Similarity	NPC93883
0.5652	Remote Similarity	NPC471356
0.5652	Remote Similarity	NPC305574
0.5625	Remote Similarity	NPC603096
0.5612	Remote Similarity	NPC232785
0.5612	Remote Similarity	NPC486139
0.551	Remote Similarity	NPC125077
0.551	Remote Similarity	NPC55532
0.55	Remote Similarity	NPC486138
0.55	Remote Similarity	NPC276838
0.5495	Remote Similarity	NPC477580
0.5444	Remote Similarity	NPC99620
0.5376	Remote Similarity	NPC290693
0.5368	Remote Similarity	NPC72260
0.5366	Remote Similarity	NPC160583
0.5326	Remote Similarity	NPC6108
0.5326	Remote Similarity	NPC89514
0.5326	Remote Similarity	NPC480915
0.5326	Remote Similarity	NPC484210
0.5306	Remote Similarity	NPC188234
0.5275	Remote Similarity	NPC473852
0.5269	Remote Similarity	NPC76572
0.5269	Remote Similarity	NPC193382
0.5217	Remote Similarity	NPC486129
0.5161	Remote Similarity	NPC486126
0.5161	Remote Similarity	NPC5311
0.5161	Remote Similarity	NPC77299
0.5161	Remote Similarity	NPC480906
0.514	Remote Similarity	NPC486150
0.5094	Remote Similarity	NPC475419
0.5053	Remote Similarity	NPC88668
0.505	Remote Similarity	NPC486143
0.505	Remote Similarity	NPC486135
0.505	Remote Similarity	NPC486142
0.505	Remote Similarity	NPC486137
0.505	Remote Similarity	NPC486149

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC297498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5675
0.1-0.2	3376
0.2-0.3	85
0.3-0.4	1
0.4-0.5	6
0.5-0.6	4
0.6-0.7	3
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
0.6437	Remote Similarity	NPD7507	Pre-clinical
0.617	Remote Similarity	NPD8377	Phase 4
0.6	Remote Similarity	NPD7516	Pre-clinical
0.5612	Remote Similarity	NPD8378	Pre-clinical
0.5612	Remote Similarity	NPD8379	Approved
0.5368	Remote Similarity	NPD8294	Phase 4
0.5053	Remote Similarity	NPD8335	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