NPASS Compound

Natural Product: NPC488610

Natural Product ID	NPC488610
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VAIYGYMQYFLHTM-SKTVXCILSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44559592
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 101104 0 0 0 0 0 0 0 0999 V2000 10.6988 -0.8811 2.1510 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2765 -0.7673 0.7572 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2056 0.6514 0.2439 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7770 1.1454 0.1855 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9187 0.2970 -0.7299 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5254 0.8834 -0.7048 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 0.1448 -1.5706 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3881 -1.3012 -1.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8853 -1.4953 0.1947 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5483 -0.8686 0.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4653 -1.4215 -0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1952 -0.7274 -0.0900 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0101 -1.1716 -0.9085 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1804 -0.4066 -0.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1623 0.4451 0.4586 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3896 -0.6409 -1.0609 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6203 -0.0468 -0.7965 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5920 -0.9681 -0.1016 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7214 -1.7748 0.8799 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5065 -0.0454 0.6922 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0527 1.0967 -0.0819 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3084 2.1970 0.9215 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8318 2.1601 2.1386 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9491 3.4586 2.8901 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2073 3.3727 4.0803 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3420 1.0136 2.9190 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6569 -0.1234 2.0229 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4445 -0.8279 1.4893 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0094 -2.0564 0.9492 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0684 -2.3550 1.6910 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9533 -3.5563 1.4813 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2354 -1.3161 2.7280 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7248 -1.4691 3.8405 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6307 0.1760 1.0726 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5530 1.4267 3.5216 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3095 1.5985 -1.2400 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4514 0.7930 -2.5003 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5925 1.7127 -3.7316 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3077 -0.4072 -2.6142 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1837 0.8757 -1.7960 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1695 1.5808 -2.4972 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2454 0.9613 -3.3115 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2191 -0.2752 -3.5234 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1725 1.7467 -4.0239 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5873 0.5687 1.6003 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7750 -1.5029 2.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4114 -1.4028 2.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4993 0.1094 2.5980 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8009 -1.4351 0.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3551 -1.0454 0.8043 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7428 1.3022 0.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7151 0.7178 -0.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8220 2.1679 -0.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3590 1.2493 1.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3236 0.4124 -1.7570 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9440 -0.7618 -0.4807 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1193 0.9336 0.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5674 1.9320 -1.0724 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5699 0.6680 -1.4634 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8469 0.2767 -2.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7137 -1.7789 -1.9305 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3783 -1.7941 -1.2744 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6089 -1.0167 0.8977 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8048 -2.5696 0.4026 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5547 0.2299 0.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2643 -1.1613 1.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3898 -2.5197 -0.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7604 -1.1905 -1.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9602 -0.9419 0.9730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3689 0.3680 -0.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1921 -1.0555 -2.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -2.2451 -0.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3293 0.6721 0.0564 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0795 -1.7077 -0.7056 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2852 -2.5440 1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9099 -2.2735 0.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2116 -1.0921 1.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0947 0.8939 -0.4815 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0192 3.1910 0.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0022 3.7154 3.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4348 4.2222 2.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6148 2.5907 4.0038 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6178 0.6745 3.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9025 -1.1561 2.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6884 -2.6731 0.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3307 -4.4593 1.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6210 -3.6617 2.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5944 -3.3929 0.5761 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5419 0.0506 1.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1353 1.7459 2.7795 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2338 2.7249 -1.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5918 2.2075 -3.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6673 1.1244 -4.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8432 2.5024 -3.7307 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0543 -0.3378 -3.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6502 -1.2556 -2.9739 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9345 -0.6679 -1.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1950 2.8055 -3.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7793 1.2320 -3.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3484 1.5504 -5.1210 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6074 0.1130 2.4686 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 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 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 30 32 1 0 32 33 2 0 27 34 1 6 26 35 1 0 21 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 37 40 1 0 40 41 1 6 41 42 1 0 42 43 2 0 42 44 1 0 20 45 1 1 40 17 1 0 28 20 1 0 40 36 1 0 32 27 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 10 65 1 0 10 66 1 0 11 67 1 0 11 68 1 0 12 69 1 0 12 70 1 0 13 71 1 0 13 72 1 0 17 73 1 1 18 74 1 6 19 75 1 0 19 76 1 0 19 77 1 0 21 78 1 6 22 79 1 0 24 80 1 0 24 81 1 0 25 82 1 0 26 83 1 1 28 84 1 1 29 85 1 0 31 86 1 0 31 87 1 0 31 88 1 0 34 89 1 0 35 90 1 0 36 91 1 6 38 92 1 0 38 93 1 0 38 94 1 0 39 95 1 0 39 96 1 0 39 97 1 0 44 98 1 0 44 99 1 0 44100 1 0 45101 1 0 M END

Standard InCHIKey	VAIYGYMQYFLHTM-SKTVXCILSA-N
Standard InCHI	InChI=1S/C36H56O9/c1-7-8-9-10-11-12-13-14-15-16-17-18-28(39)44-32-23(3)34(42)26(29-33(5,6)36(29,32)45-24(4)38)20-25(21-37)31(41)35(43)27(34)19-22(2)30(35)40/h19-20,23,26-27,29,31-32,37,41-43H,7-18,21H2,1-6H3/t23-,26+,27+,29-,31-,32-,34-,35-,36-/m1/s1
SMILES	CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@]2([C@@H](C=C(CO)[C@H]([C@]3([C@H]2C=C(C)C3=O)O)O)[C@@H]2C(C)(C)[C@]12OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	632.39	Volume:	662.916 ? Van der Waals volume.
Dense:	0.954	LogP:	4.807 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.086 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.973 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	21.0
TPSA:	150.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.189	Fsp³:	0.806
MCE-18:	80.769 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.464	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.201	Promiscuous compounds:	0.447

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.241	MDCK Permeability:	-4.693
Pgp-inhibitor:	0.074	Pgp-substrate:	0.938
PAMPA:	0.844 ? 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):	0.864
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.971
Plasma Protein Binding (PPB):	97.156%	Volume Distribution (VD):	0.554
Fu:	3.863% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.009	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.99
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.072 ? 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):

3.139

Half-life (T1/2):

1.364

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.456
Human Hepatotoxicity (H-HT):	0.699	Drug-induced Liver Injury (DILI):	0.75
AMES Toxicity:	0.613	Rat Oral Acute Toxicity:	0.287
Maximum Recommended Daily Dose:	0.28	Skin Sensitization:	1.0
Carcinogencity:	0.821	Eye Corrosion:	0.01
Eye Irritation:	0.76	Respiratory Toxicity:	0.829
Drug-induced Neurotoxicity:	0.031	Ototoxicity:	0.502
Hematotoxicity:	0.638	Drug-induced Nephrotoxicity:	0.909
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.22
A549 Cytotoxicity:	0.908	Hek293 Cytotoxicity:	0.483
BCF:	1.945 ? 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:	5.654 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.855 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.371 ? 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
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	Latex	n.a.	n.a.	PMID[6481361]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22060	Hippomane mancinella	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
Activity	2

Activity Type	# Activity
Organism	2

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.01	ug	PMID[6481361]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	96.0	%	PMID[6481361]

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 NPC488610 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	15994
0.1-0.2	30577
0.2-0.3	3081
0.3-0.4	91
0.4-0.5	71
0.5-0.6	24
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
0.7857	Intermediate Similarity	NPC488611
0.7429	Intermediate Similarity	NPC5991
0.7429	Intermediate Similarity	NPC196500
0.7429	Intermediate Similarity	NPC471108
0.7429	Intermediate Similarity	NPC5989
0.7051	Intermediate Similarity	NPC11410
0.7051	Intermediate Similarity	NPC600144
0.6806	Remote Similarity	NPC275696
0.6806	Remote Similarity	NPC255081
0.6575	Remote Similarity	NPC485737
0.6486	Remote Similarity	NPC19464
0.6447	Remote Similarity	NPC22628
0.625	Remote Similarity	NPC171905
0.6234	Remote Similarity	NPC600005
0.6133	Remote Similarity	NPC485734
0.6118	Remote Similarity	NPC600480
0.6104	Remote Similarity	NPC484252
0.6053	Remote Similarity	NPC486561
0.5949	Remote Similarity	NPC484333
0.593	Remote Similarity	NPC603807
0.5733	Remote Similarity	NPC606275
0.56	Remote Similarity	NPC472397
0.5581	Remote Similarity	NPC479001
0.5581	Remote Similarity	NPC479002
0.5556	Remote Similarity	NPC607335
0.5556	Remote Similarity	NPC610849
0.5455	Remote Similarity	NPC472758
0.5432	Remote Similarity	NPC10721
0.5385	Remote Similarity	NPC471125
0.5349	Remote Similarity	NPC138641
0.5349	Remote Similarity	NPC611243
0.5309	Remote Similarity	NPC243902
0.5301	Remote Similarity	NPC145238
0.5301	Remote Similarity	NPC609983
0.5256	Remote Similarity	NPC157252
0.5244	Remote Similarity	NPC478999
0.5185	Remote Similarity	NPC471128
0.5125	Remote Similarity	NPC145182
0.5065	Remote Similarity	NPC600179
0.5065	Remote Similarity	NPC602150
0.5057	Remote Similarity	NPC482199
0.5057	Remote Similarity	NPC482197

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488610 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6321
0.1-0.2	2742
0.2-0.3	86
0.3-0.4	1
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