NPASS Compound

Natural Product: NPC479742

Natural Product ID	NPC479742
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IFPMSAOPSQVFLA-YZIDFNLCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 98103 0 0 0 0 0 0 0 0999 V2000 -7.8338 2.5354 -0.8020 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1472 1.7822 0.0239 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8192 0.7539 0.8506 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6834 -0.1628 1.3102 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8092 -0.5373 0.1008 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9880 -1.7154 0.4977 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8262 -1.2787 1.3500 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8967 -0.3103 0.7819 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4400 0.6181 1.9042 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5944 0.5962 -0.2113 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8364 1.3951 -0.9735 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3655 1.4802 -0.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7835 0.3137 -0.1982 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6347 -0.0248 -0.5925 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7684 -0.6185 -1.9589 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4457 1.2380 -0.5793 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 1.2491 0.4588 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3657 -0.0034 0.4218 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5636 -1.2599 0.5904 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1372 -2.4130 -0.1879 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7597 -1.7249 2.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3118 -0.7651 2.9310 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1357 -0.9937 0.4304 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3095 -2.2816 0.3677 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1454 -2.0964 0.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7269 -0.8277 -0.0315 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3003 -1.1270 -1.4284 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2393 -0.0517 -0.6816 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6246 0.0261 -0.5776 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0361 0.1395 0.5556 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3912 -0.0309 -1.7723 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6622 0.0974 -1.8651 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5966 0.3468 -0.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8543 -0.2740 -0.9771 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9231 -0.0910 -0.1629 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7913 0.7591 0.9110 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5854 1.3853 1.1097 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4933 1.1835 0.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8792 0.9493 1.7484 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9236 1.4895 1.6826 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0482 0.6565 -0.3889 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6789 1.9089 0.1821 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2552 3.1757 -0.5236 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7858 -1.0256 -0.9213 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9049 -0.4795 -2.0473 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5854 -2.1177 -0.6126 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9278 2.4204 -0.8999 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4233 3.3078 -1.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5830 0.1854 0.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2736 1.1898 1.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1190 0.2623 2.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1575 -1.1112 1.6328 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6326 -2.3264 1.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7514 -2.4354 -0.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3622 -0.7611 2.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4221 -2.1750 1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6199 0.1996 2.5102 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2937 0.7008 2.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2972 1.6472 1.5662 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2938 2.0627 -1.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9188 1.6036 -1.9605 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1742 2.4682 -0.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6250 0.7474 0.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2564 -1.5900 -2.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3935 0.0195 -2.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8352 -0.7645 -2.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7851 2.0864 -0.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8472 1.4859 -1.5841 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1779 2.1260 0.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0342 0.0823 1.3011 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4009 -2.2164 -1.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5330 -3.3026 0.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1361 -2.6275 0.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8629 -1.8530 2.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3024 -2.6859 2.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9782 -0.6041 3.6588 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8032 -0.5522 1.4251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6525 -2.8055 -0.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6745 -2.9496 1.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6316 -2.9776 -0.0436 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4248 -2.2840 1.5470 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8604 -0.4848 -2.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3713 -0.9403 -1.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1251 -2.1624 -1.7414 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7913 -0.2096 -2.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0564 -0.0019 -2.9259 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9927 -0.9560 -1.8200 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8785 -0.6063 -0.3482 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4408 2.0678 1.9538 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6045 1.7769 0.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4510 0.1841 2.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2335 2.1693 1.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2529 0.7199 -1.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4085 2.0552 1.2507 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9935 3.9518 -0.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2862 3.5326 -0.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3926 3.1670 -1.6027 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0123 -2.7054 -1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 18 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 17 40 1 0 10 41 1 0 41 42 1 0 42 43 1 0 5 44 1 6 44 45 2 0 44 46 1 0 42 2 1 0 41 5 1 0 26 8 1 0 38 33 1 0 26 13 1 0 23 14 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 6 53 1 0 6 54 1 0 7 55 1 0 7 56 1 0 9 57 1 0 9 58 1 0 9 59 1 0 11 60 1 0 12 61 1 0 12 62 1 0 13 63 1 1 15 64 1 0 15 65 1 0 15 66 1 0 16 67 1 0 16 68 1 0 17 69 1 6 18 70 1 1 20 71 1 0 20 72 1 0 20 73 1 0 21 74 1 0 21 75 1 0 22 76 1 0 23 77 1 1 24 78 1 0 24 79 1 0 25 80 1 0 25 81 1 0 27 82 1 0 27 83 1 0 27 84 1 0 31 85 1 0 32 86 1 0 34 87 1 0 35 88 1 0 37 89 1 0 38 90 1 0 39 91 1 0 40 92 1 0 41 93 1 6 42 94 1 1 43 95 1 0 43 96 1 0 43 97 1 0 46 98 1 0 M END

Standard InCHIKey	IFPMSAOPSQVFLA-YZIDFNLCSA-N
Standard InCHI	InChI=1S/C39H52O7/c1-23-15-18-39(34(44)45)20-19-37(5)27(32(39)24(23)2)12-13-30-35(3)21-28(42)33(36(4,22-40)29(35)16-17-38(30,37)6)46-31(43)14-9-25-7-10-26(41)11-8-25/h7-12,14,24,28-30,32-33,40-42H,1,13,15-22H2,2-6H3,(H,44,45)/b14-9-/t24-,28+,29+,30+,32-,33-,35-,36-,37+,38+,39-/m0/s1
SMILES	C=C1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)OC(=O)/C=Cc3ccc(cc3)O)O)[C@@H]2[C@H]1C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	632.37	Volume:	672.201 ? Van der Waals volume.
Dense:	0.941	LogP:	4.198 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.542 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.421 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	36.0
TPSA:	124.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.158	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.339	Fsp³:	0.641
MCE-18:	161.719 ? 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:	0.98	Fluc inhibitor:	0.98 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.184 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.029 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.113	Promiscuous compounds:	0.108

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.777	MDCK Permeability:	-5.188
Pgp-inhibitor:	0.055	Pgp-substrate:	0.001
PAMPA:	1.0 ? 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%):	0.913	30% Bioavailability (F30%):	0.497
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.782
Plasma Protein Binding (PPB):	95.912%	Volume Distribution (VD):	-0.353
Fu:	2.972% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.881	BCRP inhibitor:	0.083
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.534
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.303
HLM stability:	0.0 ? 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):

3.113

Half-life (T1/2):

1.357

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.067
Human Hepatotoxicity (H-HT):	0.598	Drug-induced Liver Injury (DILI):	0.163
AMES Toxicity:	0.101	Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.209	Skin Sensitization:	0.999
Carcinogencity:	0.142	Eye Corrosion:	0.003
Eye Irritation:	0.687	Respiratory Toxicity:	0.619
Drug-induced Neurotoxicity:	0.082	Ototoxicity:	0.652
Hematotoxicity:	0.04	Drug-induced Nephrotoxicity:	0.907
Genotoxicity:	0.111	RPMI-8226 Immunitoxicity:	0.029
A549 Cytotoxicity:	0.576	Hek293 Cytotoxicity:	0.335
BCF:	0.607 ? 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:	3.794 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.53 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.753 ? 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
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[18481026]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	root	n.a.	PMID[19336935]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32315181]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26333	Actinidia arguta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26333	Actinidia arguta	Species	Actinidiaceae	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
Inhibition	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	Inhibition	=	41.4	%	PMID[32315181]

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 NPC479742 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	7213
0.1-0.2	36506
0.2-0.3	5414
0.3-0.4	550
0.4-0.5	118
0.5-0.6	29
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324798
0.8556	High Similarity	NPC178093
0.7957	Intermediate Similarity	NPC479739
0.7849	Intermediate Similarity	NPC304110
0.7849	Intermediate Similarity	NPC27518
0.7849	Intermediate Similarity	NPC611516
0.7789	Intermediate Similarity	NPC479745
0.7526	Intermediate Similarity	NPC479740
0.7526	Intermediate Similarity	NPC479741
0.7368	Intermediate Similarity	NPC605663
0.7292	Intermediate Similarity	NPC25491
0.6796	Remote Similarity	NPC118033
0.6667	Remote Similarity	NPC479744
0.6667	Remote Similarity	NPC482052
0.6634	Remote Similarity	NPC482051
0.6633	Remote Similarity	NPC22676
0.65	Remote Similarity	NPC172311
0.6381	Remote Similarity	NPC601567
0.6381	Remote Similarity	NPC606631
0.6364	Remote Similarity	NPC171007
0.6364	Remote Similarity	NPC190849
0.6321	Remote Similarity	NPC481234
0.6321	Remote Similarity	NPC479431
0.6214	Remote Similarity	NPC479747
0.6214	Remote Similarity	NPC479746
0.598	Remote Similarity	NPC101863
0.5769	Remote Similarity	NPC198621
0.5769	Remote Similarity	NPC216940
0.5761	Remote Similarity	NPC20235
0.5761	Remote Similarity	NPC299996
0.5755	Remote Similarity	NPC482049
0.5755	Remote Similarity	NPC482050
0.566	Remote Similarity	NPC132126
0.5652	Remote Similarity	NPC25299
0.5652	Remote Similarity	NPC481322
0.5631	Remote Similarity	NPC26045
0.5631	Remote Similarity	NPC477874
0.5607	Remote Similarity	NPC475482
0.56	Remote Similarity	NPC470617
0.56	Remote Similarity	NPC470616
0.5579	Remote Similarity	NPC230151
0.5566	Remote Similarity	NPC54627
0.5566	Remote Similarity	NPC249817
0.549	Remote Similarity	NPC485587
0.5484	Remote Similarity	NPC127689
0.5437	Remote Similarity	NPC173569
0.5421	Remote Similarity	NPC488214
0.5273	Remote Similarity	NPC610795
0.5234	Remote Similarity	NPC488215
0.5204	Remote Similarity	NPC233012
0.5185	Remote Similarity	NPC262970
0.5094	Remote Similarity	NPC475138
0.5093	Remote Similarity	NPC477873
0.5086	Remote Similarity	NPC481235

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3673
0.1-0.2	5382
0.2-0.3	92
0.3-0.4	2
0.4-0.5	1
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