NPASS Compound

Natural Product: NPC253591

Natural Product ID	NPC253591
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dichapetalin K
IUPAC Name	n.a.
Synonyms	Dichapetalin K
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502745
PubChem CID	11585309
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 95102 0 0 0 0 0 0 0 0999 V2000 -11.6885 -0.4777 1.2941 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3095 -0.4871 -0.0469 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8318 -0.1969 -0.1624 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1241 0.0155 0.9321 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7270 0.2961 0.9210 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2827 1.4429 0.2286 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8807 1.3704 0.3238 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0374 2.2815 0.1364 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4743 -0.0206 0.7026 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7905 -0.7570 0.3848 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3990 -0.5647 -0.1754 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0776 -1.9570 0.3045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9439 -1.7604 1.2348 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1853 -0.5115 0.8185 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1149 0.1711 -0.0903 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4749 0.7578 -1.2912 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1761 0.9689 -1.4120 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2963 0.6043 -0.2935 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7826 -0.6813 0.2986 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7300 -1.8252 -0.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0776 -1.1052 1.4708 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1166 -0.3222 2.5877 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5450 -1.1305 1.1345 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9212 0.2406 0.6274 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1658 0.6321 -0.6175 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5681 -0.0823 -1.8462 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5204 2.1159 -0.8382 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9850 2.0915 -1.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8395 1.3008 -0.5667 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3961 0.4073 0.5358 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9386 1.0270 1.8266 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1387 -0.9289 0.3985 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5035 -0.5961 0.5618 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9152 -0.0557 -0.6695 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2638 1.2852 -0.9368 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3843 0.0524 -0.6312 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1575 -0.3440 -1.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5426 -0.2506 -1.6833 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1973 0.2501 -0.5790 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4392 0.6475 0.4896 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0694 0.5515 0.4650 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5838 0.3559 -0.5332 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2090 0.8747 0.6188 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7641 0.7564 1.2409 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1741 -0.1487 -1.4714 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5459 -1.3532 1.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5267 -1.4936 -0.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8968 0.3149 -0.5578 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6792 -0.0351 1.8921 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3586 0.4684 1.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3327 -0.1545 1.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7890 -0.8869 -0.6919 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8706 -1.6918 0.9696 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8053 -0.6160 -1.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9503 -2.3792 0.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9111 -2.6674 -0.5180 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3786 -1.5186 2.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2969 -2.6276 1.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1110 1.0387 -2.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7624 1.4049 -2.3225 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4097 1.3811 0.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5153 -2.6038 -0.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9794 -1.4872 -1.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2255 -2.3870 -0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2151 -2.1531 1.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2174 -0.9082 3.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0863 -1.2564 2.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8555 -1.9507 0.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5585 0.9597 1.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7097 -0.0128 -2.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -1.1019 -1.7217 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 0.4725 -2.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3918 2.6932 0.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9606 2.5297 -1.6803 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3382 2.7312 -2.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0445 0.9954 1.7589 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5541 2.0741 1.9410 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6016 0.3836 2.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0441 -1.3581 -0.5965 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8955 -1.6014 1.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5527 -0.7591 -1.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3668 1.4672 -2.0350 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8483 2.0846 -0.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6734 -0.7392 -2.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1599 -0.5612 -2.5224 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9189 1.0401 1.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4448 0.8633 1.3079 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2989 0.8748 0.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8334 1.9140 0.7850 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9455 0.2991 1.5448 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5158 0.7195 2.0750 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2887 1.7417 1.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9888 0.1217 -2.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8670 -1.1741 -1.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4118 0.6109 -1.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 14 13 1 1 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 1 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 42 43 1 0 15 44 1 1 3 45 1 0 10 5 1 0 15 11 1 0 25 18 1 0 35 29 1 0 41 36 1 0 44 14 1 0 19 14 1 0 30 24 1 0 1 46 1 0 2 47 1 0 2 48 1 0 4 49 1 0 5 50 1 1 9 51 1 1 10 52 1 0 10 53 1 0 11 54 1 6 12 55 1 0 12 56 1 0 13 57 1 0 13 58 1 0 16 59 1 0 17 60 1 0 18 61 1 1 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 1 22 66 1 0 23 67 1 0 23 68 1 0 24 69 1 1 26 70 1 0 26 71 1 0 26 72 1 0 27 73 1 0 27 74 1 0 28 75 1 0 31 76 1 0 31 77 1 0 31 78 1 0 32 79 1 0 32 80 1 0 34 81 1 6 35 82 1 0 35 83 1 0 37 84 1 0 38 85 1 0 40 86 1 0 41 87 1 0 43 88 1 0 43 89 1 0 43 90 1 0 44 91 1 0 44 92 1 0 45 93 1 0 45 94 1 0 45 95 1 0 M END

Standard InCHIKey	TUJRURFPAUTAHC-OJWYEGDGSA-N
Standard InCHI	InChI=1S/C39H50O6/c1-23(20-40)16-27-18-28(34(42)45-27)29-11-15-39-21-38(29,39)14-12-31-35(2)13-10-25-17-30(24-6-8-26(43-5)9-7-24)44-22-36(25,3)32(35)19-33(41)37(31,39)4/h6-10,12,14,16,27-33,40-41H,11,13,15,17-22H2,1-5H3/b23-16+/t27-,28-,29-,30-,31+,32+,33+,35+,36-,37-,38+,39+/m0/s1
SMILES	OC/C(=C/[C@@H]1OC(=O)[C@@H](C1)[C@@H]1CC[C@@]23[C@]1(C=C[C@H]1[C@@]3(C)[C@H](O)C[C@@H]3[C@]1(C)CC=C1[C@]3(C)CO[C@@H](C1)c1ccc(cc1)OC)C2)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	614.36	Volume:	648.934 ? Van der Waals volume.
Dense:	0.947	LogP:	3.438 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.28 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.103 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	40.0
TPSA:	85.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	8.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.283	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.831	Fsp³:	0.667
MCE-18:	184.385 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.929	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.058	Promiscuous compounds:	0.245

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.893	MDCK Permeability:	-4.669
Pgp-inhibitor:	0.674	Pgp-substrate:	0.399
PAMPA:	0.162 ? 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%):	0.378	30% Bioavailability (F30%):	0.68
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.715
Plasma Protein Binding (PPB):	95.37%	Volume Distribution (VD):	0.06
Fu:	3.63% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.72
BSEP inhibitor:	0.962

ADMET: Metabolism

CYP1A2-inhibitor:	0.017	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.932	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.059	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.006	CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.193 ? 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):

9.15

Half-life (T1/2):

0.831

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.194
Human Hepatotoxicity (H-HT):	0.955	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.895	Rat Oral Acute Toxicity:	0.763
Maximum Recommended Daily Dose:	0.957	Skin Sensitization:	0.997
Carcinogencity:	0.894	Eye Corrosion:	0.0
Eye Irritation:	0.068	Respiratory Toxicity:	0.919
Drug-induced Neurotoxicity:	0.895	Ototoxicity:	0.556
Hematotoxicity:	0.7	Drug-induced Nephrotoxicity:	0.969
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.342
A549 Cytotoxicity:	0.973	Hek293 Cytotoxicity:	0.826
BCF:	1.863 ? 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:	4.208 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.826 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.214 ? 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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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
ED50	5
mortality	1

Activity Type	# Activity
Cell line	5
Organism	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
NPT1034	Cell line	Lu1	Homo sapiens	ED50	=	1.0	ug ml-1	PubChem BioAssay data set
NPT858	Cell line	LNCaP	Homo sapiens	ED50	=	2.6	ug ml-1	PMID[12617583]
NPT2345	Cell line	SW626	Homo sapiens	ED50	=	3.0	ug ml-1	DOI[10.6019/CHEMBL1201861]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[12565964]
NPT737	Cell line	HUVEC	Homo sapiens	ED50	=	2.2	ug ml-1	PMID[12565964]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	mortality	=	4.4	%	PMID[24597894]

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 NPC253591 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	8283
0.1-0.2	39037
0.2-0.3	2498
0.3-0.4	11
0.4-0.5	14
0.5-0.6	8
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8764	High Similarity	NPC243893
0.8065	Intermediate Similarity	NPC261659
0.7113	Intermediate Similarity	NPC262324
0.7041	Intermediate Similarity	NPC601361
0.701	Intermediate Similarity	NPC79921
0.6238	Remote Similarity	NPC471864
0.61	Remote Similarity	NPC608970
0.5676	Remote Similarity	NPC600616
0.5524	Remote Similarity	NPC609154
0.5285	Remote Similarity	NPC471861
0.5161	Remote Similarity	NPC471859
0.5159	Remote Similarity	NPC471860
0.5133	Remote Similarity	NPC471862
0.5044	Remote Similarity	NPC600667
0.5044	Remote Similarity	NPC609073

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC253591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3741
0.1-0.2	5352
0.2-0.3	57
0.3-0.4	0
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