NPASS Compound

Natural Product: NPC573409

Natural Product ID	NPC573409
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R},4~{a}~{S},6~{a}~{R},6~{a}~{S},8~{a}~{R},10~{S},12~{a}~{R},14~{a}~{S},14~{b}~{R})-10-hydroxy-2,4~{a},6~{a},9,9,12~{a},14~{a}-heptamethyl-1,3,4,5,6,6~{a},8,8~{a},10,11,12,13,14,14~{b}-tetradecahydropicene-2-carboxylic acid
IUPAC Name	(2~{R},4~{a}~{S},6~{a}~{R},6~{a}~{S},8~{a}~{R},10~{S},12~{a}~{R},14~{a}~{S},14~{b}~{R})-10-hydroxy-2,4~{a},6~{a},9,9,12~{a},14~{a}-heptamethyl-1,3,4,5,6,6~{a},8,8~{a},10,11,12,13,14,14~{b}-tetradecahydropicene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 81 85 0 0 0 0 0 0 0 0999 V2000 5.4881 -0.6661 -1.7030 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0787 -0.2487 -0.2749 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9771 0.8894 0.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4523 -1.4232 0.6028 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1185 -0.9941 1.7669 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2124 -2.1960 0.9312 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2507 -1.3415 1.7277 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8770 -0.0837 0.9683 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0561 1.0707 1.8985 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3948 -0.2403 0.5543 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5123 -0.1728 1.7515 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8847 0.3235 1.5313 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3248 0.0222 0.1264 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1866 -1.4477 -0.0415 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7866 0.3793 -0.0895 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6439 -0.2484 0.9739 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0861 -0.4141 0.6333 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7656 0.9380 0.8974 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6685 -1.3518 1.6309 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1793 -2.4254 1.2544 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6732 -1.0882 2.9925 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3684 -0.9246 -0.7283 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2510 -0.9193 -1.6917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2561 0.2230 -1.4806 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0764 1.4611 -1.8826 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1556 -0.0216 -2.4874 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8031 0.4053 -2.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5048 0.8657 -0.7692 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7275 2.3319 -0.7511 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9685 0.7055 -0.4680 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8525 1.4143 -1.1395 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3232 1.3425 -0.9478 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6346 0.0335 -0.3276 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3628 -1.3407 -1.6406 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6418 -1.2532 -2.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7535 0.2037 -2.3105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5718 1.8860 -0.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9425 0.8680 -0.5010 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3369 0.8392 1.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1587 -2.1230 0.1078 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0357 -1.6233 2.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7545 -2.5201 -0.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4646 -3.0713 1.5337 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6830 -1.1284 2.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3570 -1.9914 1.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9589 0.7221 2.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1017 1.4277 1.7938 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4112 1.9369 1.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4030 -1.2343 0.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5556 -1.0833 2.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9795 0.6180 2.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5420 -0.2014 2.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9906 1.4171 1.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6606 -1.7690 -0.9560 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7250 -1.9861 0.8139 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1798 -1.9440 -0.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8296 1.4852 0.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6339 0.4055 1.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 -1.2047 1.3808 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3718 1.2309 -0.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0197 1.7357 1.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4557 0.9137 1.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2431 -1.5583 3.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2589 -0.3369 -1.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7679 -1.9832 -0.6873 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7068 -0.6991 -2.7103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7650 -1.8902 -1.8795 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5031 1.9673 -2.7147 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0626 1.2639 -2.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0531 2.2238 -1.0531 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4977 0.4989 -3.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1318 -1.1038 -2.8248 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4376 1.2191 -2.8458 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0411 -0.4173 -2.3615 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3535 2.7072 -1.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1751 2.8535 0.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7261 2.7314 -0.7766 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5100 2.1389 -1.9314 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7975 1.4980 -1.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5893 2.2269 -0.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1695 -0.7539 -0.9990 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 2 0 19 21 1 0 17 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 2 1 0 33 8 1 0 30 10 1 0 28 13 1 0 24 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 6 5 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 9 46 1 0 9 47 1 0 9 48 1 0 10 49 1 6 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 14 54 1 0 14 55 1 0 14 56 1 0 15 57 1 1 16 58 1 0 16 59 1 0 18 60 1 0 18 61 1 0 18 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 29 75 1 0 29 76 1 0 29 77 1 0 31 78 1 0 32 79 1 0 32 80 1 0 33 81 1 6 M END

Standard InCHIKey	GQYYMZGTKQDPNR-HPKRVGODSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h8,19,21-23,31H,9-18H2,1-7H3,(H,32,33)/t19-,21-,22+,23-,26+,27+,28+,29+,30-/m0/s1
SMILES	CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H]5C[C@](C)(C(=O)O)CC[C@]5(C)CC[C@]4(C)C3=CC[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	3.983 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.417 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.651 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.409	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.781	Fsp³:	0.9
MCE-18:	105.368 ? 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:	0.778	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.473	Promiscuous compounds:	0.076

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.232	MDCK Permeability:	-4.895
Pgp-inhibitor:	0.015	Pgp-substrate:	0.019
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):	0.0
20% Bioavailability (F20%):	0.383	30% Bioavailability (F30%):	0.009
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.638	MRP1:	0.98
Plasma Protein Binding (PPB):	86.7%	Volume Distribution (VD):	-0.241
Fu:	12.085% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.658
BSEP inhibitor:	0.846

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.275	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.879
HLM stability:	0.089 ? 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):

3.641

Half-life (T1/2):

1.299

ADMET: Toxicity

hERG Blockers:	0.101	hERG Blockers (10um):	0.134
Human Hepatotoxicity (H-HT):	0.619	Drug-induced Liver Injury (DILI):	0.28
AMES Toxicity:	0.135	Rat Oral Acute Toxicity:	0.378
Maximum Recommended Daily Dose:	0.795	Skin Sensitization:	0.844
Carcinogencity:	0.836	Eye Corrosion:	0.008
Eye Irritation:	0.385	Respiratory Toxicity:	0.896
Drug-induced Neurotoxicity:	0.048	Ototoxicity:	0.642
Hematotoxicity:	0.235	Drug-induced Nephrotoxicity:	0.583
Genotoxicity:	0.501	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.064	Hek293 Cytotoxicity:	0.265
BCF:	1.502 ? 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:	4.013 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.431 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.884 ? 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
NPO57248	Tripterygium wilfordii var.regelii	Genus	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC573409 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	21058
0.1-0.2	24220
0.2-0.3	3526
0.3-0.4	758
0.4-0.5	209
0.5-0.6	56
0.6-0.7	13
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
0.7778	Intermediate Similarity	NPC171203
0.7778	Intermediate Similarity	NPC307426
0.7778	Intermediate Similarity	NPC98442
0.7778	Intermediate Similarity	NPC242468
0.6912	Remote Similarity	NPC263393
0.6522	Remote Similarity	NPC155120
0.6522	Remote Similarity	NPC288833
0.6471	Remote Similarity	NPC7260
0.6471	Remote Similarity	NPC210037
0.6471	Remote Similarity	NPC120968
0.6471	Remote Similarity	NPC227467
0.6471	Remote Similarity	NPC273621
0.6143	Remote Similarity	NPC472240
0.6143	Remote Similarity	NPC262858
0.6056	Remote Similarity	NPC104545
0.6	Remote Similarity	NPC142361
0.6	Remote Similarity	NPC474684
0.5972	Remote Similarity	NPC4036
0.5972	Remote Similarity	NPC65120
0.5972	Remote Similarity	NPC145067
0.5972	Remote Similarity	NPC233455
0.5972	Remote Similarity	NPC158030
0.5972	Remote Similarity	NPC474525
0.5942	Remote Similarity	NPC477872
0.5915	Remote Similarity	NPC480720
0.589	Remote Similarity	NPC46441
0.589	Remote Similarity	NPC474529
0.5857	Remote Similarity	NPC260385
0.5857	Remote Similarity	NPC110094
0.5694	Remote Similarity	NPC470375
0.5694	Remote Similarity	NPC470376
0.5634	Remote Similarity	NPC480946
0.5634	Remote Similarity	NPC187722
0.5634	Remote Similarity	NPC130577
0.5634	Remote Similarity	NPC142415
0.5634	Remote Similarity	NPC102683
0.5556	Remote Similarity	NPC182797
0.5556	Remote Similarity	NPC263272
0.5556	Remote Similarity	NPC51700
0.5556	Remote Similarity	NPC88716
0.5556	Remote Similarity	NPC68160
0.5556	Remote Similarity	NPC52169
0.5556	Remote Similarity	NPC488562
0.5556	Remote Similarity	NPC606443
0.5541	Remote Similarity	NPC474964
0.5507	Remote Similarity	NPC328052
0.5467	Remote Similarity	NPC78580
0.5455	Remote Similarity	NPC290598
0.5455	Remote Similarity	NPC30590
0.5432	Remote Similarity	NPC476878
0.5417	Remote Similarity	NPC610937
0.5405	Remote Similarity	NPC202728
0.5405	Remote Similarity	NPC158059
0.5405	Remote Similarity	NPC293564
0.5294	Remote Similarity	NPC221647
0.5278	Remote Similarity	NPC95246
0.527	Remote Similarity	NPC474537
0.5263	Remote Similarity	NPC476064
0.5211	Remote Similarity	NPC470224
0.52	Remote Similarity	NPC228784
0.52	Remote Similarity	NPC324341
0.52	Remote Similarity	NPC601810
0.5172	Remote Similarity	NPC476887
0.5143	Remote Similarity	NPC235341
0.5143	Remote Similarity	NPC30166
0.5139	Remote Similarity	NPC470077
0.5139	Remote Similarity	NPC125399
0.5139	Remote Similarity	NPC486522
0.5139	Remote Similarity	NPC470049
0.5135	Remote Similarity	NPC112866
0.5068	Remote Similarity	NPC486523
0.5067	Remote Similarity	NPC18872
0.5067	Remote Similarity	NPC290614

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC573409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6213
0.1-0.2	2869
0.2-0.3	59
0.3-0.4	3
0.4-0.5	5
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
0.5972	Remote Similarity	NPD7515	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