NPASS Compound

Natural Product: NPC72638

Natural Product ID	NPC72638
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Aleuritolic Acid
IUPAC Name	(4aS,6aR,6bR,8aR,10S,12aR,14aS,14bS)-10-hydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,6a,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	Aleuritolic Acid; Maprounic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL258249
PubChem CID	161527
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

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 6.6863 -0.0317 -1.1574 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6478 0.4891 -0.3419 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8603 1.4167 -1.1708 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4030 1.5182 -0.8739 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7535 0.1252 -0.6924 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4923 -0.4253 0.4834 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9492 -0.6808 0.2481 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5301 -0.8678 1.6674 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2249 -1.9758 -0.4743 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7885 -1.5821 1.1278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5232 -0.9565 1.7468 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6583 -0.6534 0.5250 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3017 0.2868 -0.4074 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4913 0.3647 -1.6796 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9603 0.5373 -1.4737 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4201 0.7498 -0.0593 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6478 -0.0063 0.9435 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1072 -0.0913 2.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4172 0.5964 2.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4101 0.1560 1.3844 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8663 0.2814 -0.0008 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7396 1.0550 -0.9486 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1289 0.5110 -0.9465 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2953 -0.7465 -1.7585 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0506 1.5538 -1.6069 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6382 0.2867 0.4740 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6767 0.9733 1.4562 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7762 -1.2320 1.7369 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5416 -2.1571 0.9416 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3757 -1.4970 2.9440 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3021 2.2354 0.2401 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2590 -1.9902 -0.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0365 -0.5337 -2.0024 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1479 0.7389 -1.5712 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2146 1.0856 0.4359 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0332 1.2334 -2.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2601 2.4711 -1.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8997 2.0045 -1.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2799 2.1065 0.0574 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4703 0.3961 1.2679 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4226 -1.8993 2.0113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1335 -0.1023 2.3474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6235 -0.6648 1.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9450 -1.8349 -1.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2973 -2.4984 -0.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7520 -2.7390 0.1715 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3809 -1.9552 1.9749 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5154 -2.3909 0.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0338 -1.7412 2.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8089 -0.0605 2.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1972 1.3180 0.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9449 1.2112 -2.2752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6840 -0.5677 -2.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5437 -0.2900 -1.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2836 1.4553 -2.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5706 -0.6236 2.9177 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8037 0.1923 3.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3323 1.6749 2.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8455 -0.7647 -0.4308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7953 2.1389 -0.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3212 0.8538 -1.9800 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1626 -1.6763 -1.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3550 -0.7710 -2.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -0.6971 -2.6708 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6581 1.6682 -2.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9612 2.5324 -1.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0936 1.1842 -1.6159 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6557 0.6577 0.6134 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5808 -0.7984 0.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5412 2.0257 1.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1695 0.8952 2.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9215 -2.3499 3.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2563 2.7342 0.4193 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 2.7921 -0.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6134 2.4425 1.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2317 -2.7632 0.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7910 -2.0004 -0.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8878 -2.4056 -0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1101 -0.5765 -2.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6087 0.1529 -2.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6106 -1.5040 -2.1827 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 7 9 1 0 6 10 1 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 16 17 1 0 17 18 2 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 23 25 1 0 23 26 1 0 26 27 1 0 20 28 1 1 28 29 2 0 28 30 1 0 16 31 1 1 12 32 1 6 5 33 1 6 7 2 1 0 17 12 1 0 27 20 1 0 13 5 1 0 21 16 1 0 1 34 1 0 2 35 1 1 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 6 40 1 1 8 41 1 0 8 42 1 0 8 43 1 0 9 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 13 51 1 1 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 21 59 1 6 22 60 1 0 22 61 1 0 24 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 32 78 1 0 33 79 1 0 33 80 1 0 33 81 1 0 M END

Standard InCHIKey	BHHPRAFMEFGOLZ-QVUWEPBXSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-25(2)16-17-30(24(32)33)15-10-21-28(6)12-8-19-26(3,4)23(31)11-14-27(19,5)20(28)9-13-29(21,7)22(30)18-25/h10,19-20,22-23,31H,8-9,11-18H2,1-7H3,(H,32,33)/t19-,20+,22-,23-,27-,28+,29+,30+/m0/s1
SMILES	O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@@]2(C1=CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	4.074 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.483 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.196 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.409	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.841	Fsp³:	0.9
MCE-18:	105.368 ? 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:	0.784	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.488	Promiscuous compounds:	0.046

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.413	MDCK Permeability:	-4.975
Pgp-inhibitor:	0.038	Pgp-substrate:	0.0
PAMPA:	0.962 ? 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%):	0.103	30% Bioavailability (F30%):	0.012
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.254	MRP1:	0.736
Plasma Protein Binding (PPB):	90.277%	Volume Distribution (VD):	-0.211
Fu:	7.277% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.583
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.302	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.986
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.581
HLM stability:	0.489 ? 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):

2.606

Half-life (T1/2):

1.373

ADMET: Toxicity

hERG Blockers:	0.069	hERG Blockers (10um):	0.1
Human Hepatotoxicity (H-HT):	0.627	Drug-induced Liver Injury (DILI):	0.381
AMES Toxicity:	0.148	Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.552	Skin Sensitization:	0.792
Carcinogencity:	0.813	Eye Corrosion:	0.023
Eye Irritation:	0.707	Respiratory Toxicity:	0.882
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.692
Hematotoxicity:	0.448	Drug-induced Nephrotoxicity:	0.71
Genotoxicity:	0.291	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.047	Hek293 Cytotoxicity:	0.2
BCF:	1.881 ? 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:	4.367 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.636 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.164 ? 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
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075783]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	leaves and stem	Nakorn Si Thammarat Province, Thailand	2004-MAR	PMID[18179177]
NPO41069	Sapium discolor	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30350995]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631436]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7561895]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6895	Elateriospermum tapos	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27192	Maprounea africana	Species	Euphorbiaceae	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	4
Activity	2

Activity Type	# Activity
Individual protein	3
Cell line	1
Single protein	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	24900.0	nM	PMID[7515410]
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	113.3	%	PMID[26508549]
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	102.6	%	PMID[26508549]
NPT22879	Single protein	DNA ligase 1	Homo sapiens	IC50	=	95.0	ug.mL-1	PMID[31499361]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell line	BV-2	Mus musculus	IC50	>	50000.0	nM	PMID[30350995]
NPT2	Others	Unspecified	n.a.	IC50	=	78700.0	nM	PMID[7515410]

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 NPC72638 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	20732
0.1-0.2	24819
0.2-0.3	3534
0.3-0.4	621
0.4-0.5	113
0.5-0.6	27
0.6-0.7	5
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
0.75	Intermediate Similarity	NPC49320
0.7333	Intermediate Similarity	NPC475708
0.7077	Intermediate Similarity	NPC475876
0.6984	Remote Similarity	NPC485428
0.6613	Remote Similarity	NPC485430
0.6508	Remote Similarity	NPC477057
0.6462	Remote Similarity	NPC30522
0.6232	Remote Similarity	NPC485422
0.5735	Remote Similarity	NPC480946
0.5735	Remote Similarity	NPC130577
0.5735	Remote Similarity	NPC142415
0.5735	Remote Similarity	NPC102683
0.5735	Remote Similarity	NPC198664
0.5667	Remote Similarity	NPC138374
0.5667	Remote Similarity	NPC34700
0.5571	Remote Similarity	NPC485429
0.5507	Remote Similarity	NPC18064
0.5362	Remote Similarity	NPC17733
0.5362	Remote Similarity	NPC470629
0.5244	Remote Similarity	NPC325032
0.5244	Remote Similarity	NPC477483
0.5217	Remote Similarity	NPC161751
0.5217	Remote Similarity	NPC474972
0.5217	Remote Similarity	NPC600543
0.5211	Remote Similarity	NPC182797
0.5211	Remote Similarity	NPC52169
0.5211	Remote Similarity	NPC488562
0.5135	Remote Similarity	NPC481311
0.5122	Remote Similarity	NPC327962
0.507	Remote Similarity	NPC187722
0.507	Remote Similarity	NPC274330
0.5068	Remote Similarity	NPC228784
0.5068	Remote Similarity	NPC324341
0.5068	Remote Similarity	NPC29765
0.5068	Remote Similarity	NPC601810

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC72638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6153
0.1-0.2	2921
0.2-0.3	71
0.3-0.4	3
0.4-0.5	2
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