NPASS Compound

Natural Product: NPC320281

Natural Product ID	NPC320281
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FRBHXYYJMYBCSK-GDWYWKMOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5320798
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 80 84 0 0 0 0 0 0 0 0999 V2000 4.3302 -2.1338 2.6080 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8899 -0.9053 1.7925 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4124 0.2027 2.2153 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9899 -1.2378 0.7280 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7201 -2.2586 -0.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6456 -1.6968 -1.5826 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4021 -0.1893 -1.3426 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3943 -0.3534 -0.2183 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7826 0.9520 0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2409 1.0345 1.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2219 1.2241 1.6885 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 0.4902 0.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2834 0.0885 0.8555 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1625 -1.2092 1.6688 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4273 -1.9215 1.9106 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1472 -2.1134 0.6521 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6014 -3.1967 0.3645 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3118 -0.9817 -0.2532 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1320 -0.0812 -0.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1593 -0.4720 -1.4673 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4622 0.8578 -1.8090 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6144 1.3151 -0.6718 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8554 1.3852 -0.9735 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1886 0.6424 -2.2740 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6517 0.4287 -2.4744 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2563 2.8384 -1.3263 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0689 2.7613 -0.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5299 -0.1863 0.2425 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7256 -1.5311 -1.6040 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9237 -0.5739 -2.5631 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0153 1.0417 1.7942 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6321 0.4889 -1.0326 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7041 -0.1646 -0.9234 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6999 1.8544 -0.8456 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3526 -3.0343 2.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5144 -2.2574 3.3549 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3178 -1.9874 3.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0830 0.2293 3.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1980 1.1390 1.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1593 -1.8731 1.1983 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7891 -2.3653 0.1270 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2290 -3.2291 -0.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5943 -1.8640 -2.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7549 -2.0529 -2.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6280 -1.0154 -0.7865 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6463 1.6579 0.1270 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5044 0.0612 2.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7289 1.8247 2.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5278 2.2956 1.7540 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5294 0.7886 2.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3057 -0.4485 0.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7055 -0.9389 2.6420 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4271 -1.8980 1.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0559 -1.5042 2.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1374 -2.9417 2.2873 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5398 0.9390 -0.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6283 -0.8106 -2.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4221 -1.2200 -1.1021 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0121 0.7386 -2.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3510 1.5404 -1.9957 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6645 -0.3072 -2.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9045 1.3139 -3.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2135 1.3157 -2.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7281 -0.3030 -3.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4716 3.3841 -1.8334 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 3.3469 -0.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1376 2.8386 -2.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2922 3.3787 0.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9299 2.7758 0.3131 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4893 3.2209 -1.3314 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4557 -0.6683 -0.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5645 -0.1200 1.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4836 0.8077 -0.2581 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7243 -2.0296 -1.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0566 -2.3587 -1.9306 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6415 -0.8486 -3.2119 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8067 1.6248 1.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3457 1.6701 2.3918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6118 0.4788 2.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6244 2.3066 -0.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 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 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 22 27 1 0 18 28 1 0 18 29 1 0 29 30 1 0 13 31 1 0 7 32 1 0 32 33 2 0 32 34 1 0 8 4 1 0 25 7 1 0 23 9 1 0 22 12 1 0 19 13 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 19 56 1 0 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 24 61 1 0 24 62 1 0 25 63 1 0 25 64 1 0 26 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 27 70 1 0 28 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 34 80 1 0 M END

Standard InCHIKey	FRBHXYYJMYBCSK-GDWYWKMOSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-18(2)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h19-22,24,31H,1,7-17H2,2-6H3,(H,33,34)/t19?,20-,21?,22?,24?,26+,27+,28?,29-,30+/m1/s1
SMILES	CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)CO)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.569 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.248 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.495 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.477	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.862	Fsp³:	0.867
MCE-18:	103.143 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.061	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.066 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.261	Promiscuous compounds:	0.057

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.163	MDCK Permeability:	-4.82
Pgp-inhibitor:	0.002	Pgp-substrate:	0.0
PAMPA:	0.028 ? 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%):	0.0	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.64

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923	MRP1:	0.999
Plasma Protein Binding (PPB):	93.718%	Volume Distribution (VD):	-0.059
Fu:	6.859% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.007
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.002
BSEP inhibitor:	0.966

ADMET: Metabolism

CYP1A2-inhibitor:	0.043	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.083	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.302	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.008	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.0
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):

6.154

Half-life (T1/2):

1.194

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.214
Human Hepatotoxicity (H-HT):	0.583	Drug-induced Liver Injury (DILI):	0.131
AMES Toxicity:	0.03	Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.664	Skin Sensitization:	0.122
Carcinogencity:	0.343	Eye Corrosion:	0.006
Eye Irritation:	0.4	Respiratory Toxicity:	0.547
Drug-induced Neurotoxicity:	0.245	Ototoxicity:	0.932
Hematotoxicity:	0.163	Drug-induced Nephrotoxicity:	0.099
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.035	Hek293 Cytotoxicity:	0.113
BCF:	1.292 ? 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:	4.537 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.968 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.633 ? 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
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	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 NPC320281 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	19199
0.1-0.2	25981
0.2-0.3	4012
0.3-0.4	509
0.4-0.5	83
0.5-0.6	33
0.6-0.7	29
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201655
0.8103	Intermediate Similarity	NPC192744
0.7742	Intermediate Similarity	NPC601275
0.75	Intermediate Similarity	NPC600004
0.7097	Intermediate Similarity	NPC264317
0.7097	Intermediate Similarity	NPC294438
0.6984	Remote Similarity	NPC488164
0.6984	Remote Similarity	NPC264005
0.697	Remote Similarity	NPC608379
0.6923	Remote Similarity	NPC474719
0.6721	Remote Similarity	NPC68828
0.6567	Remote Similarity	NPC611139
0.6515	Remote Similarity	NPC4309
0.6515	Remote Similarity	NPC16377
0.6471	Remote Similarity	NPC606728
0.6462	Remote Similarity	NPC488506
0.6462	Remote Similarity	NPC220498
0.6324	Remote Similarity	NPC488165
0.6324	Remote Similarity	NPC160506
0.6308	Remote Similarity	NPC80590
0.6301	Remote Similarity	NPC606354
0.6269	Remote Similarity	NPC151191
0.6212	Remote Similarity	NPC24772
0.6212	Remote Similarity	NPC213832
0.619	Remote Similarity	NPC246445
0.6164	Remote Similarity	NPC602512
0.6143	Remote Similarity	NPC600907
0.6119	Remote Similarity	NPC271974
0.6119	Remote Similarity	NPC195395
0.6119	Remote Similarity	NPC247312
0.6087	Remote Similarity	NPC486704
0.6056	Remote Similarity	NPC603461
0.6	Remote Similarity	NPC478841
0.6	Remote Similarity	NPC488166
0.6	Remote Similarity	NPC605397
0.597	Remote Similarity	NPC211162
0.597	Remote Similarity	NPC183374
0.5942	Remote Similarity	NPC474511
0.5942	Remote Similarity	NPC475061
0.5909	Remote Similarity	NPC119743
0.5882	Remote Similarity	NPC277399
0.5821	Remote Similarity	NPC30583
0.5789	Remote Similarity	NPC611262
0.5735	Remote Similarity	NPC291373
0.5714	Remote Similarity	NPC488213
0.5694	Remote Similarity	NPC606727
0.5641	Remote Similarity	NPC486709
0.5634	Remote Similarity	NPC603784
0.5571	Remote Similarity	NPC2783
0.5556	Remote Similarity	NPC602147
0.5493	Remote Similarity	NPC269360
0.5432	Remote Similarity	NPC486699
0.5342	Remote Similarity	NPC173089
0.5342	Remote Similarity	NPC169933
0.5342	Remote Similarity	NPC601176
0.5342	Remote Similarity	NPC607677
0.5301	Remote Similarity	NPC290349
0.5205	Remote Similarity	NPC158141
0.52	Remote Similarity	NPC148964
0.5176	Remote Similarity	NPC248287
0.5176	Remote Similarity	NPC234548
0.5172	Remote Similarity	NPC51947
0.5139	Remote Similarity	NPC606726
0.5116	Remote Similarity	NPC475138
0.5111	Remote Similarity	NPC487492
0.507	Remote Similarity	NPC476071
0.5057	Remote Similarity	NPC8102
0.5057	Remote Similarity	NPC66894

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC320281 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4777
0.1-0.2	4225
0.2-0.3	143
0.3-0.4	2
0.4-0.5	0
0.5-0.6	1
0.6-0.7	1
0.7-0.8	1
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
0.7097	Intermediate Similarity	NPD7520	Phase 1
0.6324	Remote Similarity	NPD8035	Phase 2
0.5476	Remote Similarity	NPD8034	Phase 2

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