NPASS Compound

Natural Product: NPC133375

Natural Product ID	NPC133375
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UOIROTIOLYEJBE-LPQPUKCKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102581112
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 100105 0 0 0 0 0 0 0 0999 V2000 3.2546 1.1213 1.8507 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9142 0.0922 0.7600 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4045 -1.2332 1.2939 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4321 0.1812 0.6423 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7240 -0.1950 1.9364 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6135 0.5189 1.8798 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -0.0863 0.7614 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8643 -1.4532 1.2682 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6762 -0.1904 -0.5497 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4662 -1.1541 -1.4060 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9071 -1.1220 -1.0972 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5290 -0.3127 -0.2549 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9893 -0.4312 -0.0766 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6302 0.3764 -1.1976 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1311 0.1765 -1.2615 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4768 -1.2284 -1.6326 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6768 0.5748 0.0945 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6025 0.9506 1.0533 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5663 1.9946 1.6603 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4950 -0.0556 1.2651 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1784 -1.2373 1.9758 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4854 0.4437 2.2451 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3505 1.2244 1.6854 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6873 0.6869 0.4736 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4822 1.8264 -0.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6319 1.0872 -2.3149 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2294 0.6001 -3.3028 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4783 2.4689 -2.2758 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7943 -0.4267 -0.5481 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1307 -1.8370 -0.8485 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4307 0.3435 -1.7311 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9220 0.1155 -1.7557 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6076 0.5312 -0.4756 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8874 -0.0121 -0.5113 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8785 0.9382 -0.6728 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8046 1.0807 0.5086 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2590 0.8694 0.1351 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3414 -0.3570 -0.7383 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4596 -0.2174 -1.9603 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9184 -1.5439 -2.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6972 -1.6599 -2.5716 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7422 -2.6382 -2.5168 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5543 0.7758 -1.8344 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6680 -0.5344 -1.1122 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9875 0.6503 1.2831 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7287 2.3996 1.0121 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3318 0.6029 2.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4572 1.8841 1.9615 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2400 1.5882 1.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1319 -1.7033 0.5729 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0201 -1.1233 2.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5833 -1.9178 1.5824 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 1.2984 0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3185 0.1250 2.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4878 -1.2860 1.9540 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1101 0.2066 2.8475 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5083 1.6149 1.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4820 -1.6915 2.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5712 -2.2840 0.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9662 -1.5252 1.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8096 0.8156 -1.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3727 -0.8154 -2.4795 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0946 -2.1860 -1.3579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5238 -1.8627 -1.6381 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3132 -1.4965 -0.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4229 1.4407 -1.0602 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2264 -0.0360 -2.1495 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5731 -1.8030 -1.9184 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2574 -1.3060 -2.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9033 -1.7684 -0.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3067 1.4774 -0.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3469 -0.2129 0.5096 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1243 -1.5051 1.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4683 -2.0865 2.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4118 -0.8882 3.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0652 1.1632 2.9077 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1749 -0.3381 3.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6668 1.4536 2.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7788 2.2471 1.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3863 2.4996 -0.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6119 1.5301 -1.5668 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6423 2.4804 -0.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4836 2.9730 -3.1666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8587 -2.0153 -1.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5871 -2.6132 -0.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1942 -2.1080 -0.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0335 -0.0222 -2.6920 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2606 1.4305 -1.6230 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1834 -0.9177 -2.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3182 0.7678 -2.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7349 1.6468 -0.5353 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3222 1.9377 -0.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5639 0.3713 1.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6849 1.7510 -0.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0751 -1.2664 -0.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1586 0.0578 -2.8153 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4074 -3.5997 -2.3623 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7393 -1.0366 -1.9801 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3111 1.4892 1.7017 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3607 2.4597 1.7812 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 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 15 26 1 0 26 27 2 0 26 28 1 0 9 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 39 43 1 0 38 44 1 0 37 45 1 0 36 46 1 0 33 2 1 0 43 35 1 0 29 4 1 0 24 7 1 0 24 12 1 0 20 13 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 4 53 1 6 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 8 58 1 0 8 59 1 0 8 60 1 0 9 61 1 6 10 62 1 0 10 63 1 0 11 64 1 0 13 65 1 6 14 66 1 0 14 67 1 0 16 68 1 0 16 69 1 0 16 70 1 0 17 71 1 0 17 72 1 0 21 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 25 80 1 0 25 81 1 0 25 82 1 0 28 83 1 0 30 84 1 0 30 85 1 0 30 86 1 0 31 87 1 0 31 88 1 0 32 89 1 0 32 90 1 0 33 91 1 1 35 92 1 6 36 93 1 1 37 94 1 6 38 95 1 1 39 96 1 6 42 97 1 0 44 98 1 0 45 99 1 0 46100 1 0 M END

Standard InCHIKey	UOIROTIOLYEJBE-LPQPUKCKSA-N
Standard InCHI	InChI=1S/C36H54O10/c1-31(2)20-10-13-36(7)21(34(20,5)12-11-23(31)45-29-26(40)24(38)25(39)27(46-29)28(41)42)9-8-18-19-16-32(3,30(43)44)17-22(37)33(19,4)14-15-35(18,36)6/h8,19-21,23-27,29,38-40H,9-17H2,1-7H3,(H,41,42)(H,43,44)/t19-,20-,21+,23-,24-,25-,26+,27-,29+,32-,33+,34-,35+,36+/m0/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5C[C@@](C)(CC(=O)[C@]5(C)CC[C@@]34C)C(=O)O)[C@@]2(C)CC[C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	646.37	Volume:	657.23 ? Van der Waals volume.
Dense:	0.983	LogP:	2.331 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.478 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.919 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	35.0
TPSA:	170.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.219	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.426	Fsp³:	0.861
MCE-18:	133.104 ? 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:	0.931	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.07 ? 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:	0.183	Promiscuous compounds:	0.117

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.67	MDCK Permeability:	-5.161
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	1.0 ? 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%):	0.055	30% Bioavailability (F30%):	0.023
50% Bioavailability (F50%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.975
Plasma Protein Binding (PPB):	79.228%	Volume Distribution (VD):	-0.561
Fu:	16.423% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.576	BCRP inhibitor:	0.001
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.0
CYP3A4-inhibitor:	0.18	CYP3A4-substrate:	0.211
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
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):

0.632

Half-life (T1/2):

2.803

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.014
Human Hepatotoxicity (H-HT):	0.669	Drug-induced Liver Injury (DILI):	0.972
AMES Toxicity:	0.266	Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.149	Skin Sensitization:	0.978
Carcinogencity:	0.362	Eye Corrosion:	0.0
Eye Irritation:	0.04	Respiratory Toxicity:	0.299
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.939
Hematotoxicity:	0.479	Drug-induced Nephrotoxicity:	0.944
Genotoxicity:	0.964	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.035	Hek293 Cytotoxicity:	0.067
BCF:	0.53 ? 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:	3.691 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.419 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.575 ? 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
NPO1211	Tachypleus tridentatus	Species	Limulidae	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 NPC133375 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	18265
0.1-0.2	27218
0.2-0.3	3309
0.3-0.4	765
0.4-0.5	233
0.5-0.6	56
0.6-0.7	9
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
0.7204	Intermediate Similarity	NPC309780
0.6923	Remote Similarity	NPC480937
0.6778	Remote Similarity	NPC286347
0.6596	Remote Similarity	NPC480938
0.6489	Remote Similarity	NPC482752
0.6429	Remote Similarity	NPC482748
0.6364	Remote Similarity	NPC157868
0.6316	Remote Similarity	NPC480943
0.6237	Remote Similarity	NPC224121
0.6042	Remote Similarity	NPC294112
0.598	Remote Similarity	NPC482747
0.598	Remote Similarity	NPC202666
0.598	Remote Similarity	NPC471961
0.598	Remote Similarity	NPC482746
0.598	Remote Similarity	NPC242015
0.5922	Remote Similarity	NPC75417
0.5882	Remote Similarity	NPC482751
0.5728	Remote Similarity	NPC473884
0.5701	Remote Similarity	NPC482734
0.5701	Remote Similarity	NPC182342
0.5701	Remote Similarity	NPC482727
0.5701	Remote Similarity	NPC471964
0.5619	Remote Similarity	NPC242840
0.5514	Remote Similarity	NPC251768
0.5514	Remote Similarity	NPC11551
0.5429	Remote Similarity	NPC472949
0.5413	Remote Similarity	NPC31193
0.5385	Remote Similarity	NPC482750
0.5377	Remote Similarity	NPC475171
0.537	Remote Similarity	NPC159309
0.537	Remote Similarity	NPC86222
0.5357	Remote Similarity	NPC120116
0.5333	Remote Similarity	NPC114441
0.5327	Remote Similarity	NPC482741
0.5327	Remote Similarity	NPC482745
0.5327	Remote Similarity	NPC482743
0.5327	Remote Similarity	NPC146753
0.5283	Remote Similarity	NPC6377
0.5283	Remote Similarity	NPC208381
0.5278	Remote Similarity	NPC471965
0.5278	Remote Similarity	NPC482749
0.5268	Remote Similarity	NPC301449
0.5268	Remote Similarity	NPC601290
0.5234	Remote Similarity	NPC482717
0.5229	Remote Similarity	NPC40775
0.5204	Remote Similarity	NPC283849
0.5204	Remote Similarity	NPC606107
0.5189	Remote Similarity	NPC275343
0.5185	Remote Similarity	NPC192791
0.5182	Remote Similarity	NPC482722
0.5182	Remote Similarity	NPC471963
0.5179	Remote Similarity	NPC114484
0.5138	Remote Similarity	NPC285091
0.5135	Remote Similarity	NPC611191
0.5091	Remote Similarity	NPC14617
0.5089	Remote Similarity	NPC482755
0.5089	Remote Similarity	NPC64715
0.5089	Remote Similarity	NPC262199
0.5048	Remote Similarity	NPC482726
0.5045	Remote Similarity	NPC475591
0.5045	Remote Similarity	NPC236870
0.5045	Remote Similarity	NPC482729
0.5045	Remote Similarity	NPC482742
0.5045	Remote Similarity	NPC482744
0.5044	Remote Similarity	NPC247315
0.5044	Remote Similarity	NPC482728

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC133375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5925
0.1-0.2	3165
0.2-0.3	51
0.3-0.4	6
0.4-0.5	2
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
0.598	Remote Similarity	NPD8328	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