NPASS Compound

Natural Product: NPC27507

Natural Product ID	NPC27507
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Al-Dihydro-Beta-Antiarin
IUPAC Name	3-[(3S,5S,8R,9S,10R,12R,13S,14S,17R)-5,12,14-trihydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419854
PubChem CID	73356794
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 84 89 0 0 0 0 0 0 0 0999 V2000 6.5718 1.6174 -1.8971 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8046 0.1231 -1.9116 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7593 -0.2272 -0.8054 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1064 -0.3192 0.5255 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8383 -1.1449 0.4650 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9775 -0.4838 -0.6058 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5841 -0.5037 -1.8297 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6911 -0.9947 -0.6159 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7202 -0.0638 -0.2438 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7967 0.2440 -1.3672 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5046 -0.4610 -1.4132 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0722 -0.8277 -0.0448 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1801 -2.3240 0.0724 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2410 -2.8940 1.2432 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5607 -0.4951 -0.1108 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4200 -1.4781 0.6448 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8448 -1.0711 0.7580 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2583 0.2713 0.3243 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3762 0.7992 1.1946 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7966 0.2292 -1.1071 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8234 1.7341 -1.4124 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3856 2.1100 -1.0071 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2061 1.3463 0.2717 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8455 0.8222 0.5320 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7557 1.8502 0.3424 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4272 1.3437 1.1375 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6002 -0.1497 1.0839 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0678 -0.4279 1.0598 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0924 -0.6996 2.2694 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4026 2.3317 1.2828 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1632 -0.2911 -1.2496 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9347 -0.9428 -0.4059 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2265 -1.2625 -0.9772 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1695 -1.8866 -0.3897 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2059 -0.7552 -2.2578 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9792 -0.1392 -2.5134 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3262 -1.3247 2.0462 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1568 -1.0564 1.6798 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8364 0.9631 0.9953 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3301 -1.4604 -1.1344 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4726 1.8589 -1.7667 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9564 2.1310 -2.8059 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1050 2.0442 -1.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2871 -0.0765 -2.9220 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5648 0.5653 -0.7677 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8117 -0.8541 1.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0651 -2.1687 0.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9079 0.5849 -0.2892 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2924 0.8915 -0.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6001 1.3533 -1.4751 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3663 0.0092 -2.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6157 -1.3749 -2.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2296 0.1547 -1.9984 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2740 -2.4947 -0.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2247 -2.8561 -0.8331 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4400 -3.5070 1.6369 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8561 -0.5778 -1.1672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0114 -1.5131 1.6791 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2664 -2.4770 0.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4157 -1.8138 0.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0620 1.7691 1.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5468 0.1357 2.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2928 1.0691 0.6730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0837 -0.2499 -1.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0035 1.9179 -2.4892 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5460 2.2162 -0.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7378 1.7953 -1.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3058 3.2006 -0.9124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8174 0.6158 1.6513 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5364 2.1209 -0.6829 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1448 2.7858 0.8319 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 1.8823 0.8516 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2446 1.6553 2.1930 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3640 -1.4609 1.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4898 0.1801 1.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3367 -0.1584 3.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1340 3.2242 0.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6829 -1.2461 0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4147 -0.7123 -3.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0797 0.9327 -2.7813 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5858 -1.5965 2.6443 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9982 -1.9727 2.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4387 1.2080 1.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9221 -1.2925 -1.9083 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 1 23 30 1 1 20 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 17 37 1 0 5 38 1 0 4 39 1 0 3 40 1 0 7 2 1 0 28 9 1 0 36 31 1 0 27 12 1 0 24 15 1 0 23 18 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 6 3 45 1 1 4 46 1 1 5 47 1 6 6 48 1 1 9 49 1 1 10 50 1 0 10 51 1 0 11 52 1 0 11 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 15 57 1 6 16 58 1 0 16 59 1 0 17 60 1 6 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 6 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 24 69 1 1 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 30 77 1 0 32 78 1 0 36 79 1 0 36 80 1 0 37 81 1 0 38 82 1 0 39 83 1 0 40 84 1 0 M END

Standard InCHIKey	KYNXIMRHBXPXLL-KRRSKSLRSA-N
Standard InCHI	InChI=1S/C29H44O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)19-10-20(31)26(2)17(15-9-21(32)38-12-15)5-8-29(26,37)18(19)4-7-28(27,36)11-16/h9,14,16-20,22-25,30-31,33-37H,3-8,10-13H2,1-2H3/t14-,16-,17+,18+,19-,20+,22-,23+,24+,25-,26-,27-,28-,29-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1CC[C@]2(CO)[C@H]3C[C@H]([C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)C1=CC(=O)OC1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.29	Volume:	550.221 ? Van der Waals volume.
Dense:	1.033	LogP:	-0.24 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.617 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.046 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	32.0
TPSA:	186.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.171	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.512	Fsp³:	0.897
MCE-18:	119.127 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.572	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? 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:	0.135	Promiscuous compounds:	0.464

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.74	MDCK Permeability:	-5.263
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.453
20% Bioavailability (F20%):	0.969	30% Bioavailability (F30%):	0.985
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.162	MRP1:	0.698
Plasma Protein Binding (PPB):	26.109%	Volume Distribution (VD):	-0.593
Fu:	78.222% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.65
OATP1B3 inhibitor:	0.388	BCRP inhibitor:	0.025
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.065	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:	0.029	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.008 ? 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):

1.057

Half-life (T1/2):

4.605

ADMET: Toxicity

hERG Blockers:	0.178	hERG Blockers (10um):	0.67
Human Hepatotoxicity (H-HT):	0.705	Drug-induced Liver Injury (DILI):	0.383
AMES Toxicity:	0.49	Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.897	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.815
Hematotoxicity:	0.29	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.91
A549 Cytotoxicity:	0.497	Hek293 Cytotoxicity:	0.978
BCF:	0.538 ? 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:	3.066 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.246 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.491 ? 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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	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

Activity Type	# Activity
Inhibition	1

Activity Type	# Activity
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	60.2	%	PMID[24033101]

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 NPC27507 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	16919
0.1-0.2	27248
0.2-0.3	5091
0.3-0.4	408
0.4-0.5	102
0.5-0.6	43
0.6-0.7	17
0.7-0.8	0
0.8-0.85	14
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	NPC471354
0.8462	Intermediate Similarity	NPC77319
0.8462	Intermediate Similarity	NPC471351
0.8462	Intermediate Similarity	NPC471355
0.8354	Intermediate Similarity	NPC9499
0.8354	Intermediate Similarity	NPC471360
0.8354	Intermediate Similarity	NPC469751
0.8354	Intermediate Similarity	NPC471361
0.8354	Intermediate Similarity	NPC86159
0.8354	Intermediate Similarity	NPC469752
0.8354	Intermediate Similarity	NPC469754
0.8354	Intermediate Similarity	NPC70542
0.8205	Intermediate Similarity	NPC157376
0.8205	Intermediate Similarity	NPC142066
0.8205	Intermediate Similarity	NPC603972
0.7683	Intermediate Similarity	NPC471353
0.7262	Intermediate Similarity	NPC179412
0.7262	Intermediate Similarity	NPC471356
0.7073	Intermediate Similarity	NPC99728
0.7073	Intermediate Similarity	NPC87250
0.7073	Intermediate Similarity	NPC244402
0.7073	Intermediate Similarity	NPC50305
0.6905	Remote Similarity	NPC17896
0.6905	Remote Similarity	NPC469755
0.6905	Remote Similarity	NPC284406
0.6905	Remote Similarity	NPC197707
0.6905	Remote Similarity	NPC251866
0.6667	Remote Similarity	NPC471359
0.6404	Remote Similarity	NPC469753
0.6395	Remote Similarity	NPC84987
0.625	Remote Similarity	NPC76572
0.625	Remote Similarity	NPC193382
0.6237	Remote Similarity	NPC471357
0.6237	Remote Similarity	NPC469757
0.6237	Remote Similarity	NPC117702
0.618	Remote Similarity	NPC83287
0.6105	Remote Similarity	NPC208193
0.6092	Remote Similarity	NPC99620
0.6	Remote Similarity	NPC264336
0.5977	Remote Similarity	NPC158344
0.5955	Remote Similarity	NPC469750
0.5914	Remote Similarity	NPC173555
0.5876	Remote Similarity	NPC469749
0.5843	Remote Similarity	NPC219085
0.5843	Remote Similarity	NPC309034
0.5795	Remote Similarity	NPC474418
0.5729	Remote Similarity	NPC475556
0.5729	Remote Similarity	NPC32793
0.5729	Remote Similarity	NPC116075
0.5729	Remote Similarity	NPC311706
0.567	Remote Similarity	NPC475629
0.5667	Remote Similarity	NPC196429
0.5604	Remote Similarity	NPC5311
0.5604	Remote Similarity	NPC77299
0.5604	Remote Similarity	NPC480906
0.5577	Remote Similarity	NPC117445
0.5577	Remote Similarity	NPC308262
0.5567	Remote Similarity	NPC240070
0.5542	Remote Similarity	NPC469794
0.55	Remote Similarity	NPC146857
0.5476	Remote Similarity	NPC196471
0.5376	Remote Similarity	NPC480914
0.5347	Remote Similarity	NPC247190
0.53	Remote Similarity	NPC59288
0.5269	Remote Similarity	NPC34390
0.5269	Remote Similarity	NPC480915
0.5253	Remote Similarity	NPC608063
0.5213	Remote Similarity	NPC10823
0.5204	Remote Similarity	NPC30483
0.5204	Remote Similarity	NPC470897
0.5158	Remote Similarity	NPC180079
0.5155	Remote Similarity	NPC480907
0.5152	Remote Similarity	NPC236973
0.5152	Remote Similarity	NPC32177
0.5152	Remote Similarity	NPC469756
0.5152	Remote Similarity	NPC275901
0.514	Remote Similarity	NPC329675
0.514	Remote Similarity	NPC194716
0.5119	Remote Similarity	NPC189588
0.51	Remote Similarity	NPC480910
0.51	Remote Similarity	NPC480909
0.5054	Remote Similarity	NPC471633

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC27507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6519
0.1-0.2	2509
0.2-0.3	105
0.3-0.4	4
0.4-0.5	5
0.5-0.6	5
0.6-0.7	3
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
0.6905	Remote Similarity	NPD7319	Approved
0.618	Remote Similarity	NPD7327	Approved
0.618	Remote Similarity	NPD7328	Phase 4
0.5914	Remote Similarity	NPD8296	Phase 4
0.5484	Remote Similarity	NPD8335	Phase 4
0.5426	Remote Similarity	NPD8380	Approved
0.5248	Remote Similarity	NPD8378	Pre-clinical
0.5248	Remote Similarity	NPD8379	Approved

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