NPASS Compound

Natural Product: NPC197963

Natural Product ID	NPC197963
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HFMLTKBZNAPPNY-HJNKUULISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101384467
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 82 87 0 0 0 0 0 0 0 0999 V2000 -7.9736 1.5870 -0.6691 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6481 0.9564 -0.2402 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9550 -0.0433 0.8289 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9770 -1.4252 0.2160 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6686 -1.7190 -0.4524 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0571 -0.4828 -1.0990 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0519 0.4268 -1.3579 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0865 -0.0163 -0.2210 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8052 -0.0795 -0.7679 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2569 1.2935 -0.8441 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7806 1.4166 -0.9140 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0432 0.4690 -0.0057 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3461 0.8833 1.4156 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5265 -0.9229 -0.3208 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2235 -2.0095 0.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7383 -1.8365 0.3122 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0069 -0.4503 0.8644 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4326 0.4805 -0.2054 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0808 1.8159 -0.2248 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5612 1.6650 -0.4466 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2327 0.5953 0.3016 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3742 1.2057 1.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8695 -0.4765 -0.5989 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8650 -1.7354 0.2103 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2505 -1.3652 1.5500 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3737 -0.1667 1.2681 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3876 0.5860 2.4674 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1963 -0.0383 -1.0808 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3817 -0.5848 -0.9121 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3601 0.2643 -1.6040 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6044 -0.0240 -1.6091 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7200 1.3251 -2.1846 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3574 1.2033 -1.8960 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6184 2.4686 -1.3978 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9769 -1.0277 0.0633 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9169 -2.7023 -1.4272 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0585 -1.5238 -0.6491 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0538 -0.0066 1.8794 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5300 0.9335 -1.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7968 2.5450 -1.1823 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6278 1.7823 0.2122 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9841 1.7569 0.1645 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9792 0.1111 1.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1405 -2.1901 1.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9664 -2.1859 0.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6371 -0.8191 -2.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9127 -0.5041 -1.8023 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6811 1.7795 -1.7729 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6921 1.9163 -0.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4697 1.3022 -1.9751 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5386 2.4520 -0.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2288 1.5879 1.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6265 0.0407 2.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4819 1.4537 1.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4663 -1.0563 -1.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1023 -2.0599 1.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0468 -2.9716 -0.1352 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0402 -1.9179 -0.7545 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1600 -2.6454 0.8980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3424 -0.3929 1.7802 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6206 0.0212 -1.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8186 2.4869 0.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0053 2.6850 -0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7638 1.4958 -1.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3863 2.3300 0.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2514 1.0381 2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3541 0.8183 0.8303 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2381 -0.6293 -1.5054 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8929 -2.1112 0.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3026 -2.5612 -0.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7637 -2.1846 2.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1124 -1.0476 2.1941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5165 0.6577 2.8792 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6140 -1.4967 -0.3648 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7650 1.1471 -2.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0698 2.1057 -1.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1355 2.1643 -2.1717 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3048 -2.0618 -0.2138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1678 -0.9131 1.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2024 -3.5166 -0.9705 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8681 -2.2582 -1.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1176 0.9067 2.2836 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 12 14 1 0 14 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 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 23 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 19 34 1 0 14 35 1 0 5 36 1 0 4 37 1 0 3 38 1 0 7 2 1 0 35 9 1 0 18 12 1 0 26 21 1 0 33 28 1 0 26 17 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 1 3 43 1 1 4 44 1 1 5 45 1 1 6 46 1 6 9 47 1 6 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 13 52 1 0 13 53 1 0 13 54 1 0 14 55 1 6 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 18 61 1 6 19 62 1 1 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 6 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 29 74 1 0 33 75 1 0 33 76 1 0 34 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 37 81 1 0 38 82 1 0 M END

Standard InCHIKey	HFMLTKBZNAPPNY-HJNKUULISA-N
Standard InCHI	InChI=1S/C29H44O9/c1-14-23(32)24(33)25(34)26(37-14)38-17-6-8-27(2)16(11-17)4-5-19-22(27)20(30)12-28(3)18(7-9-29(19,28)35)15-10-21(31)36-13-15/h10,14,16-20,22-26,30,32-35H,4-9,11-13H2,1-3H3/t14-,16-,17-,18+,19+,20+,22+,23-,24+,25+,26-,27-,28+,29-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2[C@@H](C[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)O)C1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.3	Volume:	532.64 ? Van der Waals volume.
Dense:	1.007	LogP:	1.182 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.856 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.134 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	32.0
TPSA:	145.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.267	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.215	Fsp³:	0.897
MCE-18:	113.455 ? 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:	0.722	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? 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:	0.121	Promiscuous compounds:	0.31

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.293	MDCK Permeability:	-5.307
Pgp-inhibitor:	0.001	Pgp-substrate:	0.901
PAMPA:	0.994 ? 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):	0.021
20% Bioavailability (F20%):	0.282	30% Bioavailability (F30%):	0.466
50% Bioavailability (F50%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075	MRP1:	0.194
Plasma Protein Binding (PPB):	48.205%	Volume Distribution (VD):	-0.539
Fu:	51.371% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.176
BSEP inhibitor:	0.216

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	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:	0.003
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.87
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.165
HLM stability:	0.001 ? 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):

1.907

Half-life (T1/2):

3.798

ADMET: Toxicity

hERG Blockers:	0.079	hERG Blockers (10um):	0.508
Human Hepatotoxicity (H-HT):	0.66	Drug-induced Liver Injury (DILI):	0.899
AMES Toxicity:	0.866	Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.815	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.984
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.852
Hematotoxicity:	0.76	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.789
A549 Cytotoxicity:	0.569	Hek293 Cytotoxicity:	0.943
BCF:	0.711 ? 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:	3.293 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.773 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.021 ? 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
NPO28394	Rohdea chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28394	Rohdea chinensis	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 NPC197963 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	13778
0.1-0.2	30195
0.2-0.3	5140
0.3-0.4	529
0.4-0.5	72
0.5-0.6	80
0.6-0.7	54
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8243	Intermediate Similarity	NPC99620
0.7564	Intermediate Similarity	NPC469750
0.7468	Intermediate Similarity	NPC76572
0.7468	Intermediate Similarity	NPC193382
0.7342	Intermediate Similarity	NPC5311
0.7	Intermediate Similarity	NPC196429
0.6782	Remote Similarity	NPC240070
0.6747	Remote Similarity	NPC83287
0.6744	Remote Similarity	NPC30483
0.6744	Remote Similarity	NPC470897
0.6707	Remote Similarity	NPC77299
0.6707	Remote Similarity	NPC480906
0.6667	Remote Similarity	NPC236973
0.6667	Remote Similarity	NPC179412
0.6667	Remote Similarity	NPC99728
0.6667	Remote Similarity	NPC471356
0.6667	Remote Similarity	NPC471353
0.6667	Remote Similarity	NPC87250
0.6667	Remote Similarity	NPC244402
0.6667	Remote Similarity	NPC50305
0.6667	Remote Similarity	NPC471633
0.6627	Remote Similarity	NPC480914
0.6506	Remote Similarity	NPC157376
0.6506	Remote Similarity	NPC17896
0.6506	Remote Similarity	NPC469755
0.6506	Remote Similarity	NPC284406
0.6506	Remote Similarity	NPC197707
0.6506	Remote Similarity	NPC251866
0.6506	Remote Similarity	NPC142066
0.6506	Remote Similarity	NPC480915
0.6506	Remote Similarity	NPC603972
0.6477	Remote Similarity	NPC292467
0.6444	Remote Similarity	NPC486143
0.6444	Remote Similarity	NPC486142
0.6444	Remote Similarity	NPC486149
0.6429	Remote Similarity	NPC199428
0.6429	Remote Similarity	NPC109448
0.6429	Remote Similarity	NPC310341
0.6322	Remote Similarity	NPC72260
0.6322	Remote Similarity	NPC480907
0.6267	Remote Similarity	NPC160583
0.619	Remote Similarity	NPC309034
0.6154	Remote Similarity	NPC264336
0.6129	Remote Similarity	NPC486146
0.6111	Remote Similarity	NPC32177
0.6111	Remote Similarity	NPC27363
0.6111	Remote Similarity	NPC469756
0.6111	Remote Similarity	NPC275901
0.6047	Remote Similarity	NPC84949
0.6047	Remote Similarity	NPC480562
0.6047	Remote Similarity	NPC74945
0.6047	Remote Similarity	NPC31354
0.6047	Remote Similarity	NPC69576
0.6044	Remote Similarity	NPC188234
0.6044	Remote Similarity	NPC480910
0.6044	Remote Similarity	NPC480909
0.6042	Remote Similarity	NPC486144
0.6042	Remote Similarity	NPC486145
0.6042	Remote Similarity	NPC486147
0.6042	Remote Similarity	NPC486148
0.5977	Remote Similarity	NPC77319
0.5977	Remote Similarity	NPC471351
0.5977	Remote Similarity	NPC471355
0.5918	Remote Similarity	NPC74259
0.5914	Remote Similarity	NPC59288
0.5914	Remote Similarity	NPC486135
0.5914	Remote Similarity	NPC486137
0.5876	Remote Similarity	NPC475590
0.5859	Remote Similarity	NPC474908
0.5851	Remote Similarity	NPC232785
0.5851	Remote Similarity	NPC486139
0.5814	Remote Similarity	NPC84987
0.5795	Remote Similarity	NPC250556
0.5758	Remote Similarity	NPC120390
0.5758	Remote Similarity	NPC475419
0.5745	Remote Similarity	NPC125077
0.5745	Remote Similarity	NPC208193
0.573	Remote Similarity	NPC9499
0.573	Remote Similarity	NPC471360
0.573	Remote Similarity	NPC469751
0.573	Remote Similarity	NPC93883
0.573	Remote Similarity	NPC471361
0.573	Remote Similarity	NPC86159
0.573	Remote Similarity	NPC469752
0.573	Remote Similarity	NPC469754
0.573	Remote Similarity	NPC70542
0.573	Remote Similarity	NPC305574
0.5714	Remote Similarity	NPC173555
0.57	Remote Similarity	NPC486134
0.57	Remote Similarity	NPC486141
0.5682	Remote Similarity	NPC480908
0.5667	Remote Similarity	NPC471354
0.5667	Remote Similarity	NPC27507
0.5625	Remote Similarity	NPC329986
0.5625	Remote Similarity	NPC140092
0.5591	Remote Similarity	NPC40749
0.5581	Remote Similarity	NPC158344
0.5579	Remote Similarity	NPC55532
0.5577	Remote Similarity	NPC286809
0.5567	Remote Similarity	NPC486138
0.5567	Remote Similarity	NPC276838
0.5556	Remote Similarity	NPC484202
0.5556	Remote Similarity	NPC486136
0.5534	Remote Similarity	NPC474423
0.5517	Remote Similarity	NPC473852
0.5474	Remote Similarity	NPC231518
0.5474	Remote Similarity	NPC488944
0.5455	Remote Similarity	NPC219085
0.5393	Remote Similarity	NPC479356
0.5393	Remote Similarity	NPC479355
0.5392	Remote Similarity	NPC117445
0.5392	Remote Similarity	NPC308262
0.5385	Remote Similarity	NPC483822
0.5368	Remote Similarity	NPC486130
0.5361	Remote Similarity	NPC469749
0.5326	Remote Similarity	NPC193893
0.5312	Remote Similarity	NPC486127
0.5281	Remote Similarity	NPC486129
0.5227	Remote Similarity	NPC474418
0.5222	Remote Similarity	NPC486126
0.5222	Remote Similarity	NPC484210
0.5208	Remote Similarity	NPC32793
0.5208	Remote Similarity	NPC116075
0.5192	Remote Similarity	NPC486150
0.5165	Remote Similarity	NPC152615
0.5155	Remote Similarity	NPC475629
0.5149	Remote Similarity	NPC479360
0.5149	Remote Similarity	NPC479359
0.5149	Remote Similarity	NPC488943
0.5149	Remote Similarity	NPC488942
0.5055	Remote Similarity	NPC99080
0.5053	Remote Similarity	NPC5883
0.5052	Remote Similarity	NPC475556
0.5052	Remote Similarity	NPC471357
0.5052	Remote Similarity	NPC469757
0.5052	Remote Similarity	NPC117702
0.5052	Remote Similarity	NPC311706
0.505	Remote Similarity	NPC475219
0.505	Remote Similarity	NPC486132
0.505	Remote Similarity	NPC486131

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC197963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5700
0.1-0.2	3299
0.2-0.3	132
0.3-0.4	5
0.4-0.5	2
0.5-0.6	8
0.6-0.7	4
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
0.6747	Remote Similarity	NPD7327	Approved
0.6747	Remote Similarity	NPD7328	Phase 4
0.6506	Remote Similarity	NPD7319	Approved
0.6322	Remote Similarity	NPD8294	Phase 4
0.5795	Remote Similarity	NPD7507	Pre-clinical
0.5714	Remote Similarity	NPD8296	Phase 4
0.5579	Remote Similarity	NPD8377	Phase 4
0.5474	Remote Similarity	NPD8033	Approved
0.5275	Remote Similarity	NPD8335	Phase 4
0.5217	Remote Similarity	NPD8380	Approved
0.5051	Remote Similarity	NPD8378	Pre-clinical
0.5051	Remote Similarity	NPD8379	Approved

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