NPASS Compound

Natural Product: NPC20235

Natural Product ID	NPC20235
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Alpha,3Alpha,23-Trihydroxyursa-12,20(30)-Dien-28-Oic Acid
IUPAC Name	(1R,4aS,6aR,6aS,6bR,8aR,9R,10S,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2088611
PubChem CID	70697438
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 -4.0554 -3.1363 -1.0388 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4417 -2.0542 -0.3893 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5774 -1.2276 -0.8807 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4606 0.1925 -0.4227 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9884 0.6228 -0.3009 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3736 0.5401 -1.6507 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9246 0.3399 -1.7598 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1639 -0.0429 -0.5542 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6659 -1.4951 -0.6714 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8870 0.0317 0.7201 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2748 0.2889 1.8861 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1667 0.5247 2.0355 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8571 0.2806 0.7479 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3236 0.6589 0.7549 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6079 2.0978 0.8657 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9218 -0.0772 1.9624 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4039 0.0353 2.0006 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0893 0.3096 0.7179 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3705 -0.1179 -0.5090 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9446 0.7097 -1.6719 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8269 -1.5535 -0.8233 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1913 -1.6045 -1.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8891 -0.0389 -0.4551 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2922 0.4858 -1.7288 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8644 0.7715 -1.7247 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1076 0.7965 -0.4619 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3882 2.2175 -0.1639 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3295 -0.3755 0.7472 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8965 -1.1679 2.5570 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3722 -0.1770 0.7783 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7676 -1.6109 0.8609 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7908 -1.8821 1.9787 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0518 2.0427 0.1240 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5236 2.3730 1.2082 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6730 3.0030 -0.6382 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2352 -3.7384 -0.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5766 -3.4242 -1.9448 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5240 -1.6937 -0.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6450 -1.3328 -1.9939 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8724 0.8299 -1.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0413 0.4501 0.4591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 1.4769 -2.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9250 -0.2677 -2.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7253 -0.4537 -2.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4881 1.2441 -2.2871 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4250 -1.9856 -1.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7078 -2.0464 0.2595 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3012 -1.5647 -1.1825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8756 0.3316 2.8127 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4114 1.4927 2.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5412 -0.2524 2.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8760 -0.8424 0.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8434 2.5435 -0.1031 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4331 2.2608 1.6229 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7670 2.7030 1.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5117 0.3691 2.9089 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5631 -1.1346 1.8757 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7127 0.8257 2.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4011 1.3822 0.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0389 0.5031 -1.6579 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8299 1.7908 -1.4720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5630 0.3794 -2.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4714 -2.2609 -0.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3399 -1.8069 -1.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4571 -2.2848 -1.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5067 -1.1034 -0.3648 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8997 1.3988 -2.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5953 -0.2594 -2.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6922 1.7534 -2.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3639 0.0370 -2.4275 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3604 2.9301 -0.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5693 2.4092 0.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3293 2.4624 -0.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0215 0.1720 1.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9846 -1.1035 3.5392 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7770 0.2850 1.7378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9283 -2.2959 1.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4536 -2.7117 1.6930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3227 -0.9618 2.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2564 -2.2361 2.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7898 3.9694 -0.3564 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 18 28 1 0 17 29 1 0 10 30 1 0 30 31 1 0 31 32 1 0 5 33 1 1 33 34 2 0 33 35 1 0 31 2 1 0 30 5 1 0 26 8 1 0 26 13 1 0 23 14 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 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 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 6 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 1 18 59 1 6 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 23 66 1 1 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 30 76 1 1 31 77 1 1 32 78 1 0 32 79 1 0 32 80 1 0 35 81 1 0 M END

Standard InCHIKey	FFMVHFPLIIYYNC-OKSSEWIBSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,18,20-24,31-33H,1,8-16H2,2-6H3,(H,34,35)/t18-,20+,21+,22+,23-,24+,26-,27-,28+,29+,30-/m0/s1
SMILES	C=C1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	2.846 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.749 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.494 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.414	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.229	Fsp³:	0.833
MCE-18:	104.945 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.799	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? 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:	0.306	Promiscuous compounds:	0.093

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.604	MDCK Permeability:	-5.136
Pgp-inhibitor:	0.001	Pgp-substrate:	0.085
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%):	0.593	30% Bioavailability (F30%):	0.115
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058	MRP1:	0.908
Plasma Protein Binding (PPB):	79.305%	Volume Distribution (VD):	-0.328
Fu:	16.078% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.165	BCRP inhibitor:	0.476
BSEP inhibitor:	0.975

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:	0.004	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

2.999

Half-life (T1/2):

1.518

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.034
Human Hepatotoxicity (H-HT):	0.464	Drug-induced Liver Injury (DILI):	0.328
AMES Toxicity:	0.155	Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.191	Skin Sensitization:	0.834
Carcinogencity:	0.623	Eye Corrosion:	0.004
Eye Irritation:	0.479	Respiratory Toxicity:	0.6
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.922
Hematotoxicity:	0.419	Drug-induced Nephrotoxicity:	0.828
Genotoxicity:	0.153	RPMI-8226 Immunitoxicity:	0.026
A549 Cytotoxicity:	0.026	Hek293 Cytotoxicity:	0.051
BCF:	0.663 ? 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:	3.522 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.197 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.361 ? 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
NPO31296	Rhododendron brachycarpum	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/BF02856638]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[18481026]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[19336935]
NPO31296	Rhododendron brachycarpum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940448]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32315181]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26333	Actinidia arguta	Species	Actinidiaceae	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
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	17400.0	nM	PMID[18298075]

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 NPC20235 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	20704
0.1-0.2	25001
0.2-0.3	3395
0.3-0.4	492
0.4-0.5	171
0.5-0.6	50
0.6-0.7	18
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299996
0.8615	High Similarity	NPC25299
0.8615	High Similarity	NPC481322
0.7794	Intermediate Similarity	NPC127689
0.7761	Intermediate Similarity	NPC32407
0.7761	Intermediate Similarity	NPC263548
0.7761	Intermediate Similarity	NPC606320
0.7681	Intermediate Similarity	NPC481318
0.7361	Intermediate Similarity	NPC481320
0.7324	Intermediate Similarity	NPC479743
0.726	Intermediate Similarity	NPC481319
0.7101	Intermediate Similarity	NPC231063
0.7101	Intermediate Similarity	NPC282395
0.7101	Intermediate Similarity	NPC173744
0.7101	Intermediate Similarity	NPC88116
0.7101	Intermediate Similarity	NPC204961
0.7101	Intermediate Similarity	NPC73004
0.7101	Intermediate Similarity	NPC609452
0.6901	Remote Similarity	NPC247139
0.6857	Remote Similarity	NPC37221
0.662	Remote Similarity	NPC71074
0.662	Remote Similarity	NPC605937
0.6301	Remote Similarity	NPC305464
0.6301	Remote Similarity	NPC19376
0.6301	Remote Similarity	NPC25848
0.6216	Remote Similarity	NPC88847
0.6216	Remote Similarity	NPC201657
0.6164	Remote Similarity	NPC472149
0.6164	Remote Similarity	NPC110308
0.6154	Remote Similarity	NPC479740
0.6154	Remote Similarity	NPC479741
0.6081	Remote Similarity	NPC145667
0.6053	Remote Similarity	NPC116457
0.6027	Remote Similarity	NPC84319
0.6027	Remote Similarity	NPC52021
0.6027	Remote Similarity	NPC599947
0.5946	Remote Similarity	NPC61543
0.5946	Remote Similarity	NPC293048
0.5946	Remote Similarity	NPC225585
0.5867	Remote Similarity	NPC259733
0.5867	Remote Similarity	NPC158371
0.5867	Remote Similarity	NPC207922
0.5867	Remote Similarity	NPC40092
0.5867	Remote Similarity	NPC87095
0.5824	Remote Similarity	NPC479739
0.5789	Remote Similarity	NPC9613
0.5761	Remote Similarity	NPC324798
0.5761	Remote Similarity	NPC479742
0.5714	Remote Similarity	NPC130520
0.5641	Remote Similarity	NPC117663
0.5634	Remote Similarity	NPC478657
0.5625	Remote Similarity	NPC230151
0.56	Remote Similarity	NPC307282
0.5526	Remote Similarity	NPC481314
0.5513	Remote Similarity	NPC481316
0.5443	Remote Similarity	NPC174663
0.5395	Remote Similarity	NPC270768
0.5395	Remote Similarity	NPC59263
0.5395	Remote Similarity	NPC210106
0.5395	Remote Similarity	NPC229281
0.5395	Remote Similarity	NPC51700
0.5395	Remote Similarity	NPC121798
0.5395	Remote Similarity	NPC88716
0.5395	Remote Similarity	NPC234346
0.5395	Remote Similarity	NPC68160
0.5385	Remote Similarity	NPC191412
0.5385	Remote Similarity	NPC114159
0.5385	Remote Similarity	NPC6818
0.5375	Remote Similarity	NPC481315
0.5366	Remote Similarity	NPC188833
0.5366	Remote Similarity	NPC96693
0.5325	Remote Similarity	NPC300351
0.5325	Remote Similarity	NPC481360
0.5316	Remote Similarity	NPC607666
0.5316	Remote Similarity	NPC608261
0.5316	Remote Similarity	NPC611078
0.5256	Remote Similarity	NPC173089
0.525	Remote Similarity	NPC600832
0.5132	Remote Similarity	NPC43686
0.5132	Remote Similarity	NPC479525
0.5128	Remote Similarity	NPC106112
0.5128	Remote Similarity	NPC261935
0.5128	Remote Similarity	NPC111214
0.5065	Remote Similarity	NPC477289
0.5063	Remote Similarity	NPC136697
0.5063	Remote Similarity	NPC477288

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC20235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6315
0.1-0.2	2772
0.2-0.3	60
0.3-0.4	2
0.4-0.5	1
0.5-0.6	0
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
		NPD

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