NPASS Compound

Natural Product: NPC473779

Natural Product ID	NPC473779
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Octahydroxanthochymol
IUPAC Name	n.a.
Synonyms	Octahydroxanthochymol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451601
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

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 102104 0 0 0 0 0 0 0 0999 V2000 -1.8792 -1.6232 -4.9066 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7578 -0.4568 -4.5361 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1835 0.2716 -3.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1255 -0.6734 -2.1682 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6075 -0.2222 -0.8596 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6135 -1.4514 0.0443 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2589 -2.4547 -0.2380 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8022 -1.4233 1.2892 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1952 -0.5215 1.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5868 0.3504 0.2416 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1462 -0.0257 -1.0110 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3982 -0.1535 -2.0299 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0077 0.5921 -0.0243 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9381 -0.5067 -0.4095 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1412 -1.6038 0.5612 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0350 -2.7437 0.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8013 -1.1181 1.8589 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1980 0.2405 -0.8312 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3430 -0.5455 -1.2907 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4358 0.5043 -1.6640 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7749 1.3221 -0.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6697 -0.2117 -2.1362 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0460 1.7208 0.6081 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2318 2.0537 -0.2591 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2589 0.9732 -0.2020 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5498 1.3707 -0.9106 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7017 0.6943 1.2190 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 3.4624 -0.1046 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0986 3.8779 1.2638 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5282 5.3538 1.2866 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3955 6.2519 0.8601 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0747 5.7199 2.6475 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8846 -0.4096 2.5338 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9356 -2.3388 2.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0402 -2.2570 3.2595 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9184 -3.3268 2.7080 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1917 -3.3959 2.2220 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0199 -4.4888 2.5419 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5895 -5.5145 3.3469 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3110 -5.4534 3.8441 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5113 -4.3898 3.5282 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8750 -6.4858 4.6577 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4457 -6.5809 3.6387 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1537 -0.9465 -4.2724 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0157 -1.9080 -5.9517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1220 -2.4690 -4.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8199 -1.2785 -4.7908 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8042 0.3236 -5.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1455 0.5604 -3.6733 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7242 1.1889 -3.2405 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3833 -1.4753 -2.5009 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0641 -1.2763 -2.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4546 1.0987 0.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0624 1.3624 -0.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6232 -1.0126 -1.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1961 -2.0556 0.8538 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4843 -3.7377 0.2237 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1704 -2.7347 -1.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9424 -2.8775 0.6648 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8961 -1.2895 1.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6276 -0.0682 2.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4442 -1.6992 2.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4445 1.0445 -0.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8458 0.8483 -1.7280 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8639 -1.1874 -0.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1315 -1.0099 -2.2936 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0850 1.1557 -2.4634 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8712 1.4408 -0.4024 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4131 0.8016 0.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2994 2.3254 -0.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3808 0.5631 -2.4806 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4352 -0.9310 -2.9504 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1005 -0.7657 -1.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2157 1.8158 1.6847 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7056 2.5443 0.3807 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7983 1.9767 -1.3133 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3302 1.5434 -0.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9700 0.4942 -1.4160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5089 2.3065 -1.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8930 -0.3860 1.3686 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0226 1.0310 2.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7381 1.1424 1.3878 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7645 4.1098 -0.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4123 3.8332 -0.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9201 3.3366 1.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2473 3.8353 2.0069 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3297 5.4508 0.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4270 5.7172 0.8802 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2827 7.1383 1.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5393 6.6499 -0.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7229 4.9286 3.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7260 6.7206 2.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1921 5.6818 2.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1193 0.4808 2.9022 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6055 -2.5919 1.6442 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0142 -4.4871 2.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4981 -4.3867 3.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1616 -6.5889 5.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2412 -7.5249 3.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6503 -0.2137 -3.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7445 -1.0222 -5.2164 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1244 -1.9099 -3.7281 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 5 4 1 6 5 6 1 0 6 7 2 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 2 0 10 13 1 6 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 14 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 10 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 9 33 1 0 8 34 1 0 34 35 2 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 40 42 1 0 39 43 1 0 2 44 1 0 11 5 1 0 41 36 1 0 25 5 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 13 53 1 0 13 54 1 0 14 55 1 6 15 56 1 0 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 18 64 1 0 19 65 1 0 19 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 21 70 1 0 22 71 1 0 22 72 1 0 22 73 1 0 23 74 1 0 23 75 1 0 24 76 1 6 26 77 1 0 26 78 1 0 26 79 1 0 27 80 1 0 27 81 1 0 27 82 1 0 28 83 1 0 28 84 1 0 29 85 1 0 29 86 1 0 30 87 1 0 31 88 1 0 31 89 1 0 31 90 1 0 32 91 1 0 32 92 1 0 32 93 1 0 33 94 1 0 37 95 1 0 38 96 1 0 41 97 1 0 42 98 1 0 43 99 1 0 44100 1 0 44101 1 0 44102 1 0 M END

Standard InCHIKey	WBWTVOZROFWACX-AKAMJVKKSA-N
Standard InCHI	InChI=1S/C38H58O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h14,16,19,22-25,27-28,39-40,42H,11-13,15,17-18,20-21H2,1-10H3/t27-,28+,37+,38-/m1/s1
SMILES	CC(CC[C@@]12C(=O)C(=C([C@](C1=O)(C[C@H](C(C)C)CCC(C)C)C[C@@H](C2(C)C)CCC(C)C)O)C(=O)c1ccc(c(c1)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.42	Volume:	674.421 ? Van der Waals volume.
Dense:	0.905	LogP:	7.577 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.697 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.31 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	19.0
TPSA:	111.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.084	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.409	Fsp³:	0.711
MCE-18:	100.923 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.725	Fluc inhibitor:	0.262 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.374 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.288	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.135	MDCK Permeability:	-4.929
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.238 ? 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%):	0.0	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.72

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148	MRP1:	0.995
Plasma Protein Binding (PPB):	96.885%	Volume Distribution (VD):	0.227
Fu:	3.168% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.549
OATP1B3 inhibitor:	0.006	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.964	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.082	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.024	CYP2D6-substrate:	0.962
CYP3A4-inhibitor:	0.29	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

4.449

Half-life (T1/2):

1.175

ADMET: Toxicity

hERG Blockers:	0.348	hERG Blockers (10um):	0.565
Human Hepatotoxicity (H-HT):	0.807	Drug-induced Liver Injury (DILI):	0.323
AMES Toxicity:	0.457	Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.292	Skin Sensitization:	0.994
Carcinogencity:	0.236	Eye Corrosion:	0.015
Eye Irritation:	0.24	Respiratory Toxicity:	0.773
Drug-induced Neurotoxicity:	0.039	Ototoxicity:	0.962
Hematotoxicity:	0.602	Drug-induced Nephrotoxicity:	0.862
Genotoxicity:	0.743	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.892	Hek293 Cytotoxicity:	0.281
BCF:	2.176 ? 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:	5.285 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.719 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.654 ? 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
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	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
Cell line	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	20000.0	nM	PMID[9513595]

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 NPC473779 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	5797
0.1-0.2	41727
0.2-0.3	2249
0.3-0.4	35
0.4-0.5	11
0.5-0.6	25
0.6-0.7	14
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
0.6618	Remote Similarity	NPC149773
0.6486	Remote Similarity	NPC294330
0.6389	Remote Similarity	NPC46242
0.6389	Remote Similarity	NPC91887
0.6389	Remote Similarity	NPC93556
0.6301	Remote Similarity	NPC297797
0.6133	Remote Similarity	NPC469857
0.6133	Remote Similarity	NPC245760
0.6027	Remote Similarity	NPC289358
0.6027	Remote Similarity	NPC4289
0.6027	Remote Similarity	NPC42384
0.6	Remote Similarity	NPC114333
0.6	Remote Similarity	NPC28592
0.6	Remote Similarity	NPC51531
0.5974	Remote Similarity	NPC469854
0.5974	Remote Similarity	NPC471971
0.5974	Remote Similarity	NPC471972
0.5974	Remote Similarity	NPC469855
0.5921	Remote Similarity	NPC165191
0.5921	Remote Similarity	NPC473479
0.5921	Remote Similarity	NPC50615
0.5921	Remote Similarity	NPC30846
0.5921	Remote Similarity	NPC141650
0.5921	Remote Similarity	NPC177501
0.5921	Remote Similarity	NPC479148
0.5897	Remote Similarity	NPC469856
0.5844	Remote Similarity	NPC479151
0.5823	Remote Similarity	NPC471970
0.5641	Remote Similarity	NPC482621
0.5641	Remote Similarity	NPC23667
0.5641	Remote Similarity	NPC157284
0.5625	Remote Similarity	NPC479146
0.557	Remote Similarity	NPC5014
0.5488	Remote Similarity	NPC482618
0.5238	Remote Similarity	NPC482617
0.5238	Remote Similarity	NPC482616
0.5185	Remote Similarity	NPC603871
0.5122	Remote Similarity	NPC237441
0.5063	Remote Similarity	NPC198803

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473779 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2839
0.1-0.2	6201
0.2-0.3	110
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