NPASS Compound

Natural Product: NPC269396

Natural Product ID	NPC269396
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Alpha-Hydroxylup-20(29)-En-30-Al
IUPAC Name	2-[(1R,3aR,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bS)-9-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-1-yl]prop-2-enal
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3109392
PubChem CID	76332076
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 -3.7968 1.9191 -3.3243 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2134 1.2141 -2.2991 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0457 1.8586 -1.3025 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3522 3.0674 -1.4336 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8783 -0.2207 -2.0977 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2135 -0.9264 -1.8545 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1199 -1.5680 -0.4834 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6352 -1.8276 -0.4238 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3068 -2.8780 -1.4192 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1231 -2.0772 0.9582 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6072 -2.0778 0.9261 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0972 -0.6919 0.4843 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5046 0.2482 1.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6790 -0.4809 -0.8751 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0321 0.6124 -1.6795 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4654 0.2709 -1.7338 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9408 0.3917 -0.3103 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4111 0.6547 -0.2225 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2275 -0.1644 -1.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6162 2.1227 -0.6412 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0452 2.5275 -0.5531 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9025 1.7550 0.3650 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2048 1.0765 1.5027 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2425 2.0763 2.6733 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0682 -0.0951 1.9909 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8183 0.6281 1.2221 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4444 -0.6782 1.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9079 -0.6683 1.9229 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4232 -0.7520 0.4680 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8171 -2.1036 -0.0282 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8739 2.6438 0.8909 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1487 -0.4251 -0.8206 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0274 2.9541 -3.4868 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1774 1.4203 -4.0562 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4241 1.3423 -0.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3673 -0.6469 -2.9853 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3476 -1.7419 -2.6169 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0731 -0.2677 -1.9593 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4107 -0.9160 0.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7063 -2.5112 -0.5296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6573 -3.6986 -1.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2413 -3.4246 -1.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8604 -2.5170 -2.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5472 -1.3404 1.6408 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4235 -3.0806 1.3307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2394 -2.3335 1.9363 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3055 -2.8687 0.2435 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5781 0.4543 1.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2475 -0.2591 2.5353 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0088 1.2490 1.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4127 -1.4292 -1.4442 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3700 0.4708 -2.7355 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1548 1.6156 -1.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4931 -0.7852 -2.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0012 0.8915 -2.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4441 1.3232 0.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9049 0.4517 -1.8177 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8647 -0.9222 -0.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5141 -0.6179 -1.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9535 2.7529 0.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2602 2.2962 -1.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5235 2.5130 -1.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0613 3.6189 -0.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5295 0.9622 -0.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6388 1.7350 3.5153 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8379 3.0418 2.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3083 2.2683 2.9189 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8429 -1.0271 1.4813 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1397 0.1437 1.9537 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8103 -0.2369 3.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1376 1.3958 1.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7392 -0.5528 2.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8606 -1.5597 1.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6648 0.3730 2.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4931 -1.4535 2.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2962 -2.4385 -0.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9035 -2.2171 -0.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6396 -2.8222 0.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6528 2.6923 0.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5899 0.2710 -0.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 2 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 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 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 22 31 1 0 14 32 1 0 32 5 1 0 32 8 1 0 29 12 1 0 29 17 1 0 26 18 1 0 1 33 1 0 1 34 1 0 3 35 1 0 5 36 1 6 6 37 1 0 6 38 1 0 7 39 1 0 7 40 1 0 9 41 1 0 9 42 1 0 9 43 1 0 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 13 48 1 0 13 49 1 0 13 50 1 0 14 51 1 6 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 1 19 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 6 24 65 1 0 24 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 1 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 32 80 1 1 M END

Standard InCHIKey	RYHMCEZDZZBPAQ-ISZJTHHZSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-19(18-31)20-10-13-27(4)16-17-29(6)21(25(20)27)8-9-23-28(5)14-12-24(32)26(2,3)22(28)11-15-30(23,29)7/h18,20-25,32H,1,8-17H2,2-7H3/t20-,21+,22-,23+,24+,25+,27+,28-,29+,30+/m0/s1
SMILES	C=C(C=O)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	496.961 ? Van der Waals volume.
Dense:	0.886	LogP:	5.862 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.652 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.338 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.364	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.897	Fsp³:	0.9
MCE-18:	101.263 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.905	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.558	Promiscuous compounds:	0.102

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.476	MDCK Permeability:	-5.032
Pgp-inhibitor:	0.874	Pgp-substrate:	0.032
PAMPA:	0.19 ? 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%):	0.409	30% Bioavailability (F30%):	0.804
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.412	MRP1:	0.789
Plasma Protein Binding (PPB):	96.619%	Volume Distribution (VD):	0.085
Fu:	3.587% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.658
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.961	CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.019	CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.368	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.925
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.927
HLM stability:	0.934 ? 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):

12.545

Half-life (T1/2):

0.509

ADMET: Toxicity

hERG Blockers:	0.044	hERG Blockers (10um):	0.153
Human Hepatotoxicity (H-HT):	0.473	Drug-induced Liver Injury (DILI):	0.223
AMES Toxicity:	0.387	Rat Oral Acute Toxicity:	0.233
Maximum Recommended Daily Dose:	0.737	Skin Sensitization:	0.917
Carcinogencity:	0.937	Eye Corrosion:	0.318
Eye Irritation:	0.88	Respiratory Toxicity:	0.883
Drug-induced Neurotoxicity:	0.033	Ototoxicity:	0.345
Hematotoxicity:	0.454	Drug-induced Nephrotoxicity:	0.622
Genotoxicity:	0.746	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.129	Hek293 Cytotoxicity:	0.491
BCF:	2.0 ? 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:	4.535 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.83 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.402 ? 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
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]

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
IC50	6

Activity Type	# Activity
Cell line	2
Non-molecular	4

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
NPT179	Cell line	A2780	Homo sapiens	IC50	>	10000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[19908853]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[24467317]

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 NPC269396 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	21533
0.1-0.2	23822
0.2-0.3	3791
0.3-0.4	536
0.4-0.5	100
0.5-0.6	45
0.6-0.7	21
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
0.82	Intermediate Similarity	NPC192638
0.82	Intermediate Similarity	NPC25511
0.82	Intermediate Similarity	NPC600137
0.7736	Intermediate Similarity	NPC248830
0.7736	Intermediate Similarity	NPC212241
0.7143	Intermediate Similarity	NPC74595
0.7143	Intermediate Similarity	NPC264665
0.7037	Intermediate Similarity	NPC97534
0.7037	Intermediate Similarity	NPC195155
0.6792	Remote Similarity	NPC142712
0.6667	Remote Similarity	NPC159497
0.6667	Remote Similarity	NPC480925
0.6667	Remote Similarity	NPC48079
0.661	Remote Similarity	NPC12774
0.6607	Remote Similarity	NPC301226
0.6491	Remote Similarity	NPC231256
0.6491	Remote Similarity	NPC178383
0.6316	Remote Similarity	NPC144075
0.6316	Remote Similarity	NPC202540
0.629	Remote Similarity	NPC607755
0.6271	Remote Similarity	NPC246956
0.6271	Remote Similarity	NPC119355
0.6167	Remote Similarity	NPC298168
0.6167	Remote Similarity	NPC143133
0.6102	Remote Similarity	NPC93662
0.6034	Remote Similarity	NPC104387
0.6034	Remote Similarity	NPC240235
0.6034	Remote Similarity	NPC14112
0.6032	Remote Similarity	NPC483720
0.6	Remote Similarity	NPC57469
0.5965	Remote Similarity	NPC80297
0.5965	Remote Similarity	NPC475727
0.5965	Remote Similarity	NPC116119
0.5926	Remote Similarity	NPC232112
0.5873	Remote Similarity	NPC472739
0.5862	Remote Similarity	NPC185536
0.5862	Remote Similarity	NPC102708
0.5833	Remote Similarity	NPC5767
0.5833	Remote Similarity	NPC475742
0.5763	Remote Similarity	NPC91573
0.569	Remote Similarity	NPC606606
0.5667	Remote Similarity	NPC42853
0.5667	Remote Similarity	NPC237460
0.5645	Remote Similarity	NPC103754
0.5645	Remote Similarity	NPC126993
0.5593	Remote Similarity	NPC43300
0.5574	Remote Similarity	NPC296701
0.5574	Remote Similarity	NPC218616
0.5507	Remote Similarity	NPC475416
0.55	Remote Similarity	NPC78067
0.55	Remote Similarity	NPC278091
0.5484	Remote Similarity	NPC305835
0.5469	Remote Similarity	NPC471900
0.5469	Remote Similarity	NPC175410
0.541	Remote Similarity	NPC58631
0.5385	Remote Similarity	NPC201406
0.5385	Remote Similarity	NPC289486
0.5385	Remote Similarity	NPC264317
0.5385	Remote Similarity	NPC294438
0.5323	Remote Similarity	NPC211009
0.5323	Remote Similarity	NPC201725
0.5312	Remote Similarity	NPC49599
0.5312	Remote Similarity	NPC49627
0.5303	Remote Similarity	NPC481321
0.5303	Remote Similarity	NPC112009
0.5303	Remote Similarity	NPC33768
0.5254	Remote Similarity	NPC35652
0.5246	Remote Similarity	NPC245869
0.5231	Remote Similarity	NPC477578
0.5231	Remote Similarity	NPC477577
0.5217	Remote Similarity	NPC488165
0.5152	Remote Similarity	NPC611062
0.5147	Remote Similarity	NPC16377
0.5079	Remote Similarity	NPC602784
0.5077	Remote Similarity	NPC603388

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC269396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6837
0.1-0.2	2237
0.2-0.3	70
0.3-0.4	5
0.4-0.5	0
0.5-0.6	1
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
0.5385	Remote Similarity	NPD7520	Phase 1

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