NPASS Compound

Natural Product: NPC576313

Natural Product ID	NPC576313
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{S},5~{S},8~{R},9~{S},10~{S},13~{R},14~{S},17~{R})-3-[(2~{S},4~{R},5~{R},6~{R})-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2~{H}-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthrene-10-carbaldehyde
IUPAC Name	(3~{S},5~{S},8~{R},9~{S},10~{S},13~{R},14~{S},17~{R})-3-[(2~{S},4~{R},5~{R},6~{R})-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2~{H}-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 80 85 0 0 0 0 0 0 0 0999 V2000 6.5394 1.5829 -2.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5528 1.5554 -0.6493 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2841 1.3545 -0.2108 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9390 0.0883 0.1963 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6149 0.1503 0.6239 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8452 -0.7389 -0.1126 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2345 -1.7395 0.8589 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7941 -2.0574 0.4367 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0091 -0.8106 0.7188 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3911 -0.7829 2.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0618 0.1054 2.9100 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2599 -0.7367 -0.1569 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0019 -2.0495 -0.1852 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2539 -1.8712 -0.9667 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 -0.9084 -0.3167 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6886 -1.5851 0.9364 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3200 -0.5023 -1.2657 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2711 0.4647 -0.6779 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3969 1.7387 -0.9956 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4489 2.3053 -0.1774 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8550 3.5073 -0.1982 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9631 1.3389 0.6484 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2532 0.1478 0.3847 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4808 0.1855 -2.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3861 0.8751 -1.5751 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5040 0.3879 -0.1229 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2189 1.3269 0.6185 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1463 0.2910 0.4870 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4514 1.6082 0.4551 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0754 1.5611 -0.1145 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7796 0.4488 0.3944 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5479 0.8567 1.4845 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7252 0.0549 -0.7493 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7659 -0.3734 1.3846 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1331 0.2913 1.3603 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0942 -0.4234 2.0289 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4769 0.4917 -0.1205 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3107 -0.7206 -0.7796 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3838 2.1892 -2.5524 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5725 1.9756 -2.5108 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6058 0.5338 -2.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8898 2.5464 -0.2582 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9925 -0.6607 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4412 -1.2932 -0.8656 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8031 -2.6840 0.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2114 -1.3559 1.8908 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 -2.4059 -0.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4510 -2.8414 1.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9909 -1.5895 2.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9099 -0.4632 -1.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0770 -2.4425 0.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3613 -2.7806 -0.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9681 -1.6589 -1.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7875 -2.8660 -0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6732 -2.0622 0.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6537 -0.9743 1.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0565 -2.4914 1.1999 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8235 -1.3742 -1.7285 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8254 2.3252 -1.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7936 -0.0976 1.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9997 -0.6047 0.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0308 0.9487 -2.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1238 -0.5239 -3.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4546 1.9796 -1.6071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4294 0.5875 -2.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3613 1.0202 1.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2885 -0.0388 1.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3951 2.0432 1.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0341 2.3556 -0.1374 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1526 1.5795 -1.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4278 2.5320 0.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5554 1.8472 1.4751 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2006 -0.6141 -1.4532 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0953 0.9494 -1.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2129 -0.2032 2.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9369 -1.4603 1.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0032 1.3068 1.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0298 -0.1791 3.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5460 0.8227 -0.1865 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1060 -1.2957 -0.7123 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 7 8 1 0 8 9 1 0 9 10 1 1 10 11 2 0 9 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 17 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 4 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 2 1 0 33 6 1 0 31 9 1 0 28 12 1 0 26 15 1 0 23 18 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 1 4 43 1 6 6 44 1 6 7 45 1 0 7 46 1 0 8 47 1 0 8 48 1 0 10 49 1 0 12 50 1 6 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 6 19 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 24 63 1 0 25 64 1 0 25 65 1 0 27 66 1 0 28 67 1 1 29 68 1 0 29 69 1 0 30 70 1 0 30 71 1 0 32 72 1 0 33 73 1 0 33 74 1 0 34 75 1 0 34 76 1 0 35 77 1 1 36 78 1 0 37 79 1 1 38 80 1 0 M END

Standard InCHIKey	QBILRDAMJUPXCX-YLADIGORSA-N
Standard InCHI	InChI=1S/C29H42O9/c1-16-25(33)22(31)12-24(37-16)38-18-3-8-27(15-30)20-4-7-26(2)19(17-11-23(32)36-14-17)6-10-29(26,35)21(20)5-9-28(27,34)13-18/h11,15-16,18-22,24-25,31,33-35H,3-10,12-14H2,1-2H3/t16-,18+,19-,20+,21-,22-,24-,25+,26-,27+,28+,29+/m1/s1
SMILES	C[C@H]1O[C@H](O[C@H]2CC[C@]3(C=O)[C@H]4CC[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.28	Volume:	530.004 ? Van der Waals volume.
Dense:	1.008	LogP:	0.696 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.449 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.169 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	142.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.241	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.323	Fsp³:	0.862
MCE-18:	114.074 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.855	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.152	Promiscuous compounds:	0.558

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.723	MDCK Permeability:	-5.117
Pgp-inhibitor:	0.0	Pgp-substrate:	0.983
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):	0.003
20% Bioavailability (F20%):	0.075	30% Bioavailability (F30%):	0.139
50% Bioavailability (F50%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.285
Plasma Protein Binding (PPB):	65.557%	Volume Distribution (VD):	-0.168
Fu:	33.174% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.012
BSEP inhibitor:	0.48

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.486
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):

3.187

Half-life (T1/2):

4.054

ADMET: Toxicity

hERG Blockers:	0.218	hERG Blockers (10um):	0.815
Human Hepatotoxicity (H-HT):	0.771	Drug-induced Liver Injury (DILI):	0.4
AMES Toxicity:	0.845	Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.942	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.991
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.782
Hematotoxicity:	0.36	Drug-induced Nephrotoxicity:	0.939
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.809
A549 Cytotoxicity:	0.877	Hek293 Cytotoxicity:	0.99
BCF:	0.571 ? 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:	3.329 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.913 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.254 ? 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
NPO17222	Hesperis matronalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO604	Erysimum crepidifolium	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17966	Erysimum helveticum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO604	Erysimum crepidifolium	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO604	Erysimum crepidifolium	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17966	Erysimum helveticum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17222	Hesperis matronalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO604	Erysimum crepidifolium	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	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 NPC576313 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	15055
0.1-0.2	30296
0.2-0.3	4229
0.3-0.4	72
0.4-0.5	95
0.5-0.6	55
0.6-0.7	36
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8611	High Similarity	NPC474418
0.8026	Intermediate Similarity	NPC17896
0.8026	Intermediate Similarity	NPC469755
0.8026	Intermediate Similarity	NPC284406
0.8026	Intermediate Similarity	NPC197707
0.8026	Intermediate Similarity	NPC251866
0.7821	Intermediate Similarity	NPC180079
0.7692	Intermediate Similarity	NPC10823
0.7662	Intermediate Similarity	NPC484211
0.7342	Intermediate Similarity	NPC6108
0.7342	Intermediate Similarity	NPC89514
0.7308	Intermediate Similarity	NPC471633
0.7215	Intermediate Similarity	NPC219085
0.7176	Intermediate Similarity	NPC608063
0.6923	Remote Similarity	NPC329636
0.6914	Remote Similarity	NPC484210
0.6875	Remote Similarity	NPC99728
0.6875	Remote Similarity	NPC87250
0.6875	Remote Similarity	NPC244402
0.6875	Remote Similarity	NPC50305
0.6854	Remote Similarity	NPC146857
0.6782	Remote Similarity	NPC32793
0.6782	Remote Similarity	NPC116075
0.6742	Remote Similarity	NPC469749
0.6707	Remote Similarity	NPC157376
0.6707	Remote Similarity	NPC34390
0.6707	Remote Similarity	NPC142066
0.6707	Remote Similarity	NPC603972
0.6706	Remote Similarity	NPC72260
0.6702	Remote Similarity	NPC329675
0.6667	Remote Similarity	NPC9499
0.6667	Remote Similarity	NPC471360
0.6667	Remote Similarity	NPC473852
0.6667	Remote Similarity	NPC469751
0.6667	Remote Similarity	NPC471361
0.6667	Remote Similarity	NPC86159
0.6667	Remote Similarity	NPC469752
0.6667	Remote Similarity	NPC469754
0.6667	Remote Similarity	NPC70542
0.6484	Remote Similarity	NPC247190
0.6404	Remote Similarity	NPC475556
0.6404	Remote Similarity	NPC311706
0.64	Remote Similarity	NPC72772
0.6395	Remote Similarity	NPC469753
0.6386	Remote Similarity	NPC84987
0.6354	Remote Similarity	NPC194716
0.6279	Remote Similarity	NPC471359
0.6145	Remote Similarity	NPC158344
0.6118	Remote Similarity	NPC469750
0.6	Remote Similarity	NPC309034
0.5977	Remote Similarity	NPC77319
0.5977	Remote Similarity	NPC484212
0.5977	Remote Similarity	NPC471351
0.5977	Remote Similarity	NPC471355
0.5882	Remote Similarity	NPC99620
0.5806	Remote Similarity	NPC475629
0.5745	Remote Similarity	NPC59288
0.5745	Remote Similarity	NPC125077
0.5714	Remote Similarity	NPC173555
0.5682	Remote Similarity	NPC84949
0.5682	Remote Similarity	NPC76572
0.5682	Remote Similarity	NPC480562
0.5682	Remote Similarity	NPC74945
0.5682	Remote Similarity	NPC31354
0.5682	Remote Similarity	NPC193382
0.5682	Remote Similarity	NPC69576
0.5682	Remote Similarity	NPC480914
0.5667	Remote Similarity	NPC471354
0.5667	Remote Similarity	NPC27507
0.5584	Remote Similarity	NPC97487
0.5568	Remote Similarity	NPC480915
0.5556	Remote Similarity	NPC483822
0.5556	Remote Similarity	NPC93883
0.5495	Remote Similarity	NPC193893
0.5444	Remote Similarity	NPC250556
0.5443	Remote Similarity	NPC10232
0.5393	Remote Similarity	NPC5311
0.5393	Remote Similarity	NPC77299
0.5393	Remote Similarity	NPC480906
0.5385	Remote Similarity	NPC484202
0.5306	Remote Similarity	NPC329986
0.5306	Remote Similarity	NPC140092
0.5281	Remote Similarity	NPC196429
0.5258	Remote Similarity	NPC55532
0.5253	Remote Similarity	NPC486138
0.5253	Remote Similarity	NPC276838
0.525	Remote Similarity	NPC196931
0.5217	Remote Similarity	NPC179412
0.5217	Remote Similarity	NPC471356
0.5217	Remote Similarity	NPC277374
0.5208	Remote Similarity	NPC188234
0.5208	Remote Similarity	NPC240070
0.5204	Remote Similarity	NPC232785
0.5204	Remote Similarity	NPC486139
0.5165	Remote Similarity	NPC199428
0.5165	Remote Similarity	NPC109448
0.5165	Remote Similarity	NPC310341
0.5146	Remote Similarity	NPC120390
0.5146	Remote Similarity	NPC74259
0.5122	Remote Similarity	NPC469794
0.5109	Remote Similarity	NPC88668
0.5109	Remote Similarity	NPC83287
0.5106	Remote Similarity	NPC480907
0.5098	Remote Similarity	NPC475590
0.5054	Remote Similarity	NPC305574

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC576313 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6021
0.1-0.2	2996
0.2-0.3	119
0.3-0.4	1
0.4-0.5	5
0.5-0.6	6
0.6-0.7	1
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	Drug ID	Developmental Stage
0.8026	Intermediate Similarity	NPD7319	Approved
0.6706	Remote Similarity	NPD8294	Phase 4
0.5714	Remote Similarity	NPD8296	Phase 4
0.5579	Remote Similarity	NPD8377	Phase 4
0.5444	Remote Similarity	NPD7507	Pre-clinical
0.5385	Remote Similarity	NPD7516	Pre-clinical
0.5109	Remote Similarity	NPD7327	Approved
0.5109	Remote Similarity	NPD7328	Phase 4

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