NPASS Compound

Natural Product: NPC77299

Natural Product ID	NPC77299
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HMPCXZPEEFWOAA-RFTNVSRNSA-N
IUPAC Name	n.a.
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 83 88 0 0 0 0 0 0 0 0999 V2000 -5.2157 1.5040 0.8410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3348 0.3230 0.4847 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3983 0.1445 1.6528 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1737 1.0230 1.4229 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4596 0.2823 0.3018 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2273 0.6163 -0.9344 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6157 -0.1834 -2.0919 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1444 0.2780 -2.1798 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5781 -0.0890 -0.9051 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0292 0.1325 -1.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7706 -0.2936 0.1655 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1732 0.2017 1.4346 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6879 0.2194 1.4965 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0059 0.6813 0.2217 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1315 2.1629 0.1770 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4356 2.6429 0.1275 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1204 0.0360 0.1289 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9711 -1.0615 0.1296 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7493 -1.2240 -1.1230 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1132 -1.7858 -0.7952 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7831 -0.6964 0.0646 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8712 -0.3792 1.2407 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4782 1.0743 1.1279 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6525 1.4573 2.2052 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7485 -1.1656 1.2371 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9744 -1.2064 0.5113 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9037 -1.9429 -1.9174 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1451 -2.1018 -2.0304 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7040 0.4450 -0.8386 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2538 -0.7038 -1.6147 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7616 -1.7499 -0.6801 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2191 -0.9232 0.5051 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6635 -0.6250 0.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5414 -0.9436 1.3994 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8791 -0.5136 1.0452 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8982 -0.6797 1.7471 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7966 0.0936 -0.1803 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4630 0.0134 -0.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2696 1.6046 -1.4484 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1682 1.2046 1.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3104 2.2385 0.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6772 2.0777 1.6435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0420 -0.9048 1.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9097 0.3475 2.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5869 1.1640 2.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5899 1.9969 1.0309 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4963 -0.8164 0.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9704 1.6640 -1.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5936 -1.2575 -1.8953 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0246 0.1197 -3.0746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3075 -0.2890 -3.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1410 1.3350 -2.4296 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3231 -1.1686 -0.7272 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2779 1.1695 -1.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4399 -0.4547 -1.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6473 -1.4194 0.1890 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5398 1.2533 1.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5790 -0.3657 2.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3962 0.8502 2.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3291 -0.8029 1.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3954 2.6653 -0.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3123 2.6506 1.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3730 3.6155 -0.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2616 -1.9531 0.1642 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9592 -0.2398 -1.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0765 -2.6813 -0.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9556 0.1834 -0.5779 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4756 -0.4663 2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0495 1.3344 0.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3826 1.7436 1.2417 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7761 2.4307 2.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5159 -1.4735 -0.2791 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9217 -2.9158 -2.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2034 -3.0223 -1.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5535 -1.1347 -2.3535 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1338 -0.3871 -2.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0143 -2.5204 -0.4005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6196 -2.3016 -1.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0109 -1.5759 1.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2473 -1.4628 2.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1622 1.0584 -0.8533 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3934 -0.5554 -1.5828 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7407 2.3983 -1.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 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 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 15 16 1 0 11 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 6 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 1 0 29 39 1 6 32 2 1 0 38 33 1 0 29 2 1 0 14 5 1 0 25 18 1 0 14 9 1 0 1 40 1 0 1 41 1 0 1 42 1 0 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 1 6 48 1 6 7 49 1 0 7 50 1 0 8 51 1 0 8 52 1 0 9 53 1 1 10 54 1 0 10 55 1 0 11 56 1 1 12 57 1 0 12 58 1 0 13 59 1 0 13 60 1 0 15 61 1 0 15 62 1 0 16 63 1 0 18 64 1 1 19 65 1 6 20 66 1 1 21 67 1 6 22 68 1 1 23 69 1 0 23 70 1 0 24 71 1 0 26 72 1 0 27 73 1 0 28 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 32 79 1 1 34 80 1 0 38 81 1 0 38 82 1 0 39 83 1 0 M END

Standard InCHIKey	HMPCXZPEEFWOAA-RFTNVSRNSA-N
Standard InCHI	InChI=1S/C29H44O10/c1-27-7-5-19-20(29(27,36)9-6-18(27)15-10-22(32)37-13-15)3-2-16-11-17(4-8-28(16,19)14-31)38-26-25(35)24(34)23(33)21(12-30)39-26/h10,16-21,23-26,30-31,33-36H,2-9,11-14H2,1H3/t16-,17-,18+,19-,20+,21+,23+,24-,25+,26+,27+,28+,29-/m0/s1
SMILES	C[C@@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](CC[C@]34CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@]2(CC[C@@H]1C1=CC(=O)OC1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.29	Volume:	541.431 ? Van der Waals volume.
Dense:	1.02	LogP:	0.487 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.123 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.463 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	32.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.208	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.186	Fsp³:	0.897
MCE-18:	110.618 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.757	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.145	Promiscuous compounds:	0.266

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.566	MDCK Permeability:	-5.145
Pgp-inhibitor:	0.0	Pgp-substrate:	0.956
PAMPA:	0.971 ? 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%):	0.123	30% Bioavailability (F30%):	0.792
50% Bioavailability (F50%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.245	MRP1:	0.291
Plasma Protein Binding (PPB):	57.435%	Volume Distribution (VD):	-0.397
Fu:	40.032% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.011
BSEP inhibitor:	0.056

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:	0.006	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.027
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):

2.625

Half-life (T1/2):

3.056

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.133
Human Hepatotoxicity (H-HT):	0.804	Drug-induced Liver Injury (DILI):	0.827
AMES Toxicity:	0.96	Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.884	Skin Sensitization:	1.0
Carcinogencity:	0.914	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.226
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.966
Hematotoxicity:	0.74	Drug-induced Nephrotoxicity:	0.964
Genotoxicity:	0.814	RPMI-8226 Immunitoxicity:	0.307
A549 Cytotoxicity:	0.784	Hek293 Cytotoxicity:	0.847
BCF:	0.579 ? 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:	3.283 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.751 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.898 ? 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
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	roots	Wadi Um Hebal, Egypt	2001-JAN	PMID[16989527]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555122]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30629433]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	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

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	5

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
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	1000.0	nM	PMID[30629433]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	300.0	nM	PMID[30629433]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	8000.0	nM	PMID[30629433]
NPT1307	Cell line	Calu-1	Homo sapiens	IC50	=	6000.0	nM	PMID[30629433]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	6000.0	nM	PMID[30629433]

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 NPC77299 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	13595
0.1-0.2	29270
0.2-0.3	5686
0.3-0.4	1063
0.4-0.5	69
0.5-0.6	73
0.6-0.7	56
0.7-0.8	0
0.8-0.85	2
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC480906
0.9041	High Similarity	NPC76572
0.9041	High Similarity	NPC193382
0.8961	High Similarity	NPC32177
0.8961	High Similarity	NPC469756
0.8961	High Similarity	NPC275901
0.8846	High Similarity	NPC480910
0.8846	High Similarity	NPC480909
0.8649	High Similarity	NPC5311
0.8625	High Similarity	NPC486135
0.8625	High Similarity	NPC486137
0.8533	High Similarity	NPC480914
0.8101	Intermediate Similarity	NPC480907
0.8023	Intermediate Similarity	NPC486136
0.7901	Intermediate Similarity	NPC30483
0.7901	Intermediate Similarity	NPC470897
0.7805	Intermediate Similarity	NPC236973
0.7711	Intermediate Similarity	NPC188234
0.7711	Intermediate Similarity	NPC240070
0.7662	Intermediate Similarity	NPC99620
0.759	Intermediate Similarity	NPC292467
0.7564	Intermediate Similarity	NPC84987
0.7529	Intermediate Similarity	NPC486143
0.7529	Intermediate Similarity	NPC486142
0.7529	Intermediate Similarity	NPC486149
0.7468	Intermediate Similarity	NPC469750
0.7442	Intermediate Similarity	NPC232785
0.7442	Intermediate Similarity	NPC486139
0.7407	Intermediate Similarity	NPC471353
0.7407	Intermediate Similarity	NPC305574
0.7326	Intermediate Similarity	NPC125077
0.7195	Intermediate Similarity	NPC483822
0.7159	Intermediate Similarity	NPC329986
0.7159	Intermediate Similarity	NPC140092
0.7159	Intermediate Similarity	NPC486146
0.7079	Intermediate Similarity	NPC486138
0.7079	Intermediate Similarity	NPC276838
0.7033	Intermediate Similarity	NPC486144
0.7033	Intermediate Similarity	NPC486145
0.7033	Intermediate Similarity	NPC486147
0.7033	Intermediate Similarity	NPC486148
0.6914	Remote Similarity	NPC196429
0.6848	Remote Similarity	NPC475590
0.6829	Remote Similarity	NPC157376
0.6829	Remote Similarity	NPC142066
0.6829	Remote Similarity	NPC603972
0.6705	Remote Similarity	NPC32793
0.6705	Remote Similarity	NPC116075
0.6702	Remote Similarity	NPC120390
0.6702	Remote Similarity	NPC74259
0.6702	Remote Similarity	NPC475419
0.6632	Remote Similarity	NPC474908
0.6632	Remote Similarity	NPC486134
0.6632	Remote Similarity	NPC486141
0.6629	Remote Similarity	NPC475629
0.6585	Remote Similarity	NPC99728
0.6585	Remote Similarity	NPC87250
0.6585	Remote Similarity	NPC244402
0.6585	Remote Similarity	NPC50305
0.6562	Remote Similarity	NPC486150
0.6517	Remote Similarity	NPC475556
0.6517	Remote Similarity	NPC311706
0.6517	Remote Similarity	NPC486130
0.6484	Remote Similarity	NPC469749
0.6444	Remote Similarity	NPC486127
0.6429	Remote Similarity	NPC17896
0.6429	Remote Similarity	NPC469755
0.6429	Remote Similarity	NPC284406
0.6429	Remote Similarity	NPC474423
0.6429	Remote Similarity	NPC197707
0.6429	Remote Similarity	NPC251866
0.6429	Remote Similarity	NPC480915
0.6386	Remote Similarity	NPC471633
0.6374	Remote Similarity	NPC208193
0.6316	Remote Similarity	NPC222875
0.6316	Remote Similarity	NPC25177
0.6264	Remote Similarity	NPC231518
0.6264	Remote Similarity	NPC264336
0.6264	Remote Similarity	NPC488944
0.6237	Remote Similarity	NPC146857
0.6237	Remote Similarity	NPC247190
0.6207	Remote Similarity	NPC179412
0.6207	Remote Similarity	NPC471356
0.6163	Remote Similarity	NPC199428
0.6163	Remote Similarity	NPC243196
0.6163	Remote Similarity	NPC109448
0.6163	Remote Similarity	NPC310341
0.6105	Remote Similarity	NPC476221
0.6105	Remote Similarity	NPC477709
0.6105	Remote Similarity	NPC486132
0.6105	Remote Similarity	NPC486131
0.6092	Remote Similarity	NPC146456
0.6092	Remote Similarity	NPC250556
0.6087	Remote Similarity	NPC610296
0.6071	Remote Similarity	NPC158344
0.6067	Remote Similarity	NPC72260
0.6042	Remote Similarity	NPC486128
0.5977	Remote Similarity	NPC84949
0.5977	Remote Similarity	NPC480562
0.5977	Remote Similarity	NPC74945
0.5977	Remote Similarity	NPC31354
0.5977	Remote Similarity	NPC69576
0.5974	Remote Similarity	NPC480913
0.593	Remote Similarity	NPC219085
0.5876	Remote Similarity	NPC479360
0.5876	Remote Similarity	NPC479359
0.5876	Remote Similarity	NPC488943
0.5876	Remote Similarity	NPC488942
0.587	Remote Similarity	NPC40749
0.5851	Remote Similarity	NPC59288
0.5814	Remote Similarity	NPC473852
0.58	Remote Similarity	NPC486140
0.58	Remote Similarity	NPC117445
0.58	Remote Similarity	NPC329675
0.58	Remote Similarity	NPC308262
0.58	Remote Similarity	NPC194716
0.5773	Remote Similarity	NPC475219
0.5747	Remote Similarity	NPC309034
0.5743	Remote Similarity	NPC486133
0.5714	Remote Similarity	NPC329905
0.5714	Remote Similarity	NPC488938
0.5714	Remote Similarity	NPC488937
0.5699	Remote Similarity	NPC27363
0.5673	Remote Similarity	NPC286809
0.5667	Remote Similarity	NPC484202
0.5667	Remote Similarity	NPC93883
0.5638	Remote Similarity	NPC479353
0.5638	Remote Similarity	NPC479354
0.5604	Remote Similarity	NPC471354
0.5604	Remote Similarity	NPC27507
0.5588	Remote Similarity	NPC329784
0.5579	Remote Similarity	NPC488941
0.5579	Remote Similarity	NPC488940
0.5556	Remote Similarity	NPC77319
0.5556	Remote Similarity	NPC471351
0.5556	Remote Similarity	NPC471355
0.5534	Remote Similarity	NPC488945
0.5534	Remote Similarity	NPC488946
0.5517	Remote Similarity	NPC474418
0.5472	Remote Similarity	NPC486152
0.5443	Remote Similarity	NPC268829
0.5443	Remote Similarity	NPC295110
0.5385	Remote Similarity	NPC83287
0.5361	Remote Similarity	NPC55532
0.5333	Remote Similarity	NPC488947
0.5326	Remote Similarity	NPC9499
0.5326	Remote Similarity	NPC471360
0.5326	Remote Similarity	NPC469751
0.5326	Remote Similarity	NPC471361
0.5326	Remote Similarity	NPC86159
0.5326	Remote Similarity	NPC469752
0.5326	Remote Similarity	NPC469754
0.5326	Remote Similarity	NPC70542
0.53	Remote Similarity	NPC479357
0.5275	Remote Similarity	NPC604978
0.5253	Remote Similarity	NPC488939
0.525	Remote Similarity	NPC187302
0.5222	Remote Similarity	NPC486129
0.5217	Remote Similarity	NPC88668
0.5185	Remote Similarity	NPC196931
0.5185	Remote Similarity	NPC10232
0.5181	Remote Similarity	NPC196471
0.5165	Remote Similarity	NPC486126
0.5165	Remote Similarity	NPC34390
0.5158	Remote Similarity	NPC173555
0.5155	Remote Similarity	NPC608063
0.5109	Remote Similarity	NPC10823
0.5054	Remote Similarity	NPC180079
0.5053	Remote Similarity	NPC488161
0.5053	Remote Similarity	NPC16569

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC77299 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5757
0.1-0.2	3236
0.2-0.3	137
0.3-0.4	5
0.4-0.5	4
0.5-0.6	5
0.6-0.7	4
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
0.6429	Remote Similarity	NPD7319	Approved
0.6264	Remote Similarity	NPD8033	Approved
0.6092	Remote Similarity	NPD7507	Pre-clinical
0.6067	Remote Similarity	NPD8294	Phase 4
0.5521	Remote Similarity	NPD8377	Phase 4
0.5385	Remote Similarity	NPD7327	Approved
0.5385	Remote Similarity	NPD7328	Phase 4
0.5158	Remote Similarity	NPD8296	Phase 4
0.5054	Remote Similarity	NPD8335	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