NPASS Compound

Natural Product: NPC82477

Natural Product ID	NPC82477
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ursan-12-En-3-One
IUPAC Name	(4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydropicen-3-one
Synonyms	alpha-amyrenone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL518475
PubChem CID	12306155
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 79 83 0 0 0 0 0 0 0 0999 V2000 -5.7181 2.1054 -0.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9252 0.9048 -1.2491 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5887 -0.3868 -0.8835 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8919 -1.1355 0.2279 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4932 -1.5791 -0.1896 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8593 -0.3984 -0.8770 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5565 0.9025 -0.5408 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7699 2.0843 -0.9972 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3847 -0.3569 -0.7331 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6789 0.1341 -1.7354 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7969 0.2632 -1.7971 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2963 0.3048 -0.4007 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7970 -0.8508 0.3783 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7060 -0.8533 0.5039 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2973 -2.2164 0.7410 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7962 -2.0998 0.9968 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0371 -0.0015 1.7076 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2001 -2.1969 -0.1502 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4272 -0.7213 1.7509 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9332 -0.7596 1.7249 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3884 0.4646 0.9705 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7606 0.6010 -0.3786 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5188 -0.0996 -1.4847 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8535 2.0925 -0.7454 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1469 2.7224 -0.3191 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1931 1.7487 0.0225 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3090 1.7106 -0.4535 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8446 0.7183 1.0473 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2011 1.4100 2.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7432 -0.4527 0.9300 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7117 -2.7446 -1.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8284 2.1186 0.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2417 3.0231 -1.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7302 2.0204 -1.2119 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8093 1.0056 -2.3347 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6079 -0.1526 -0.5128 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7198 -1.0363 -1.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4689 -2.0738 0.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9084 -0.5867 1.1673 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1506 -0.5510 -1.9672 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8212 1.0128 0.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8387 2.2391 -2.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2615 2.9953 -0.5450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7520 2.0432 -0.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2949 0.4756 -2.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0068 1.1850 -2.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1558 -0.5929 -2.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7926 1.2056 0.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -2.8657 -0.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9031 -2.7049 1.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0425 -1.6402 1.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1229 -3.1782 1.1340 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6117 1.0318 1.6091 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0940 0.1430 1.9062 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6328 -0.5362 2.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9637 -2.3300 -1.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7000 -2.9675 0.4750 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2752 -2.4398 -0.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1230 -1.5392 2.4310 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1831 0.2893 2.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2375 -0.5690 2.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3899 -1.6907 1.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9172 1.3019 1.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0243 -1.0426 -1.8157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5297 0.5169 -2.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5903 -0.2548 -1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9885 2.6118 -0.2767 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8038 2.1866 -1.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5686 3.4034 -1.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9869 3.3511 0.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6530 2.3683 2.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2843 1.6368 2.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9472 0.7213 3.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5234 -0.2888 0.1466 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3514 -0.6388 1.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2702 -1.4140 0.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4125 -3.7048 -0.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0407 -2.5831 -2.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7428 -2.8184 -1.5032 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 6 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 1 13 18 1 6 13 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 5 31 1 6 7 2 1 0 14 9 1 0 28 21 1 0 16 5 1 0 22 12 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 6 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 6 40 1 6 7 41 1 1 8 42 1 0 8 43 1 0 8 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 1 15 49 1 0 15 50 1 0 16 51 1 0 16 52 1 0 17 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 1 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 M END

Standard InCHIKey	DIFWJJFSELKWGA-IPQOMUISSA-N
Standard InCHI	InChI=1S/C30H48O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h9,19-20,22-23,25H,10-18H2,1-8H3/t19-,20+,22+,23-,25+,27-,28+,29-,30-/m1/s1
SMILES	C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	424.37	Volume:	488.171 ? Van der Waals volume.
Dense:	0.869	LogP:	6.207 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.444 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.012 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	27.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.358	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.676	Fsp³:	0.9
MCE-18:	98.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.955	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.037 ? 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:	0.68	Promiscuous compounds:	0.1

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.309	MDCK Permeability:	-4.9
Pgp-inhibitor:	0.997	Pgp-substrate:	0.0
PAMPA:	0.664 ? 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%):	0.096	30% Bioavailability (F30%):	0.04
50% Bioavailability (F50%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.84	MRP1:	0.97
Plasma Protein Binding (PPB):	97.649%	Volume Distribution (VD):	0.278
Fu:	3.236% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.692
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.169
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.009	CYP2C8-inhibitor:	0.654
HLM stability:	0.718 ? 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):

9.842

Half-life (T1/2):

0.103

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.2
Human Hepatotoxicity (H-HT):	0.664	Drug-induced Liver Injury (DILI):	0.501
AMES Toxicity:	0.312	Rat Oral Acute Toxicity:	0.469
Maximum Recommended Daily Dose:	0.601	Skin Sensitization:	0.884
Carcinogencity:	0.921	Eye Corrosion:	0.194
Eye Irritation:	0.785	Respiratory Toxicity:	0.769
Drug-induced Neurotoxicity:	0.277	Ototoxicity:	0.39
Hematotoxicity:	0.793	Drug-induced Nephrotoxicity:	0.797
Genotoxicity:	0.937	RPMI-8226 Immunitoxicity:	0.065
A549 Cytotoxicity:	0.395	Hek293 Cytotoxicity:	0.569
BCF:	2.63 ? 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:	4.334 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.972 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.917 ? 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
NPO64536	Barleria albostellata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446958]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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
NPO64536	Barleria albostellata	n.a.	Stems	2.18	n.a.	n.a.	%	PMID[37446958]

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
Activity	4
IC50	2
ED50	1

Activity Type	# Activity
Individual protein	5
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Activity	=	100.0	%	PMID[31774676]
NPT324	Individual protein	Cyclooxygenase-1	Ovis aries	Activity	=	100.0	%	PMID[31774676]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	>	40000.0	nM	PMID[31774676]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	Activity	=	94.0	%	PMID[31774676]
NPT570	Individual protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	100.0	%	PMID[31774676]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell line	B16	Mus musculus	ED50	>	50.0	uM	PMID[12027734]
NPT319	Cell line	B16	Mus musculus	IC50	=	40300.0	nM	PMID[12027734]

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 NPC82477 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	28681
0.1-0.2	18188
0.2-0.3	2350
0.3-0.4	472
0.4-0.5	129
0.5-0.6	23
0.6-0.7	11
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
0.7544	Intermediate Similarity	NPC606009
0.7544	Intermediate Similarity	NPC610552
0.7407	Intermediate Similarity	NPC142754
0.6897	Remote Similarity	NPC274724
0.65	Remote Similarity	NPC133954
0.6441	Remote Similarity	NPC290495
0.6349	Remote Similarity	NPC263272
0.6316	Remote Similarity	NPC27765
0.6316	Remote Similarity	NPC122418
0.6316	Remote Similarity	NPC491014
0.629	Remote Similarity	NPC274050
0.629	Remote Similarity	NPC162632
0.6071	Remote Similarity	NPC469770
0.6066	Remote Similarity	NPC3915
0.5968	Remote Similarity	NPC267517
0.5938	Remote Similarity	NPC329943
0.5846	Remote Similarity	NPC474845
0.5735	Remote Similarity	NPC105189
0.5645	Remote Similarity	NPC471897
0.5556	Remote Similarity	NPC95594
0.5556	Remote Similarity	NPC107039
0.5538	Remote Similarity	NPC267691
0.541	Remote Similarity	NPC190035
0.5385	Remote Similarity	NPC40552
0.5362	Remote Similarity	NPC193750
0.5303	Remote Similarity	NPC80784
0.5303	Remote Similarity	NPC477579
0.5294	Remote Similarity	NPC38754
0.5294	Remote Similarity	NPC184006
0.5224	Remote Similarity	NPC86372
0.5217	Remote Similarity	NPC173089
0.5161	Remote Similarity	NPC474488
0.5156	Remote Similarity	NPC40394
0.5147	Remote Similarity	NPC480926
0.5077	Remote Similarity	NPC602872
0.5075	Remote Similarity	NPC127855
0.507	Remote Similarity	NPC476064

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC82477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7780
0.1-0.2	1329
0.2-0.3	37
0.3-0.4	4
0.4-0.5	0
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