NPASS Compound

Natural Product: NPC486695

Natural Product ID	NPC486695
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LHQDSEISPPGRMR-LJGZSNSNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	132525294
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 98103 0 0 0 0 0 0 0 0999 V2000 -6.2765 0.1045 3.3525 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1442 0.4114 2.7392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9068 0.0563 3.5292 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0234 1.0831 1.4192 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3872 1.3835 0.8700 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6008 0.3156 -0.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2263 0.3589 -0.8587 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8940 -0.8523 -1.6510 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4389 -0.8184 -2.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4875 -0.6895 -0.8442 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4633 -1.9068 0.0039 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9933 0.4698 -0.0032 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0166 0.8994 1.0391 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7385 1.3214 0.2864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2341 0.0333 -0.3257 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1151 -0.3682 -1.4614 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2416 0.6794 -2.5304 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6137 -1.5833 -2.1989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8909 -1.4447 -2.4877 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5383 -1.3463 -1.1748 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9810 -1.5045 -1.0413 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8354 -0.9623 -2.1329 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3000 -2.9967 -0.8694 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -0.8582 0.3186 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0063 -0.1780 0.7499 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3084 -0.8488 1.8281 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0542 -0.2508 2.9320 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -2.1708 1.8076 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1738 -2.7691 2.8850 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2289 -0.0136 -0.5395 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8317 1.1544 -1.2498 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3565 0.0185 0.1126 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5627 -0.0306 0.7465 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7703 -0.9225 1.5940 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5918 0.9541 0.4292 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3899 1.9506 -0.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3477 2.8911 -0.8186 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5612 2.8454 -0.1839 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8003 1.8622 0.7556 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8299 0.9330 1.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0513 1.8739 1.3607 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5430 3.7893 -0.4904 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3703 0.1994 0.4251 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9767 1.6102 -1.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9521 1.5888 -2.8306 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7535 2.8598 -1.0154 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2712 0.2656 2.9779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2673 -0.3670 4.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4294 -0.8420 3.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2145 0.8928 3.6336 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2126 -0.2322 4.5710 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4651 2.0590 1.5311 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2163 1.4049 1.5697 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4215 2.4056 0.3866 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7032 -0.6509 0.2857 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4066 0.5886 -0.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4603 -0.8654 -2.6044 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1701 -1.7457 -1.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1665 -1.7110 -2.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2984 0.1201 -2.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8043 -1.7698 1.0502 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0949 -2.6924 -0.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4823 -2.4113 0.1239 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0387 1.3359 -0.7310 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7303 0.0365 1.6763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 1.7777 1.5558 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9891 2.0904 -0.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0177 1.7076 0.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4073 -0.7427 0.4847 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2084 1.0456 -2.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8318 1.5490 -2.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5179 0.1760 -3.5047 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0832 -1.6292 -3.2210 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7619 -2.5428 -1.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1666 -2.3636 -3.0476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0099 -0.5964 -3.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 -2.1136 -0.5093 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2507 -0.9806 -3.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2866 0.0265 -1.9194 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7205 -1.6480 -2.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3918 -3.0854 -0.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8346 -3.3617 0.0711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9008 -3.5881 -1.6974 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5790 -1.5896 1.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3033 0.8359 1.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4611 -3.8403 2.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9237 -2.6973 2.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3731 -2.2539 3.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7951 1.5103 -0.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1198 0.9819 -2.2944 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1595 2.0388 -1.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4275 2.0086 -1.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1354 3.6661 -1.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0577 0.1734 1.8023 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7597 1.1934 1.1774 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5292 4.7209 -0.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5771 -0.8483 0.7361 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0098 3.4260 -1.4435 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 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 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 25 30 1 0 30 31 1 6 24 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 39 41 1 0 38 42 1 0 12 43 1 0 7 44 1 6 44 45 2 0 44 46 1 0 43 4 1 0 43 7 1 0 16 10 1 0 30 20 1 0 40 35 1 0 30 15 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 1 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 8 57 1 0 8 58 1 0 9 59 1 0 9 60 1 0 11 61 1 0 11 62 1 0 11 63 1 0 12 64 1 6 13 65 1 0 13 66 1 0 14 67 1 0 14 68 1 0 15 69 1 1 17 70 1 0 17 71 1 0 17 72 1 0 18 73 1 0 18 74 1 0 19 75 1 0 19 76 1 0 20 77 1 1 22 78 1 0 22 79 1 0 22 80 1 0 23 81 1 0 23 82 1 0 23 83 1 0 24 84 1 1 25 85 1 1 29 86 1 0 29 87 1 0 29 88 1 0 31 89 1 0 31 90 1 0 31 91 1 0 36 92 1 0 37 93 1 0 40 94 1 0 41 95 1 0 42 96 1 0 43 97 1 1 46 98 1 0 M END

Standard InCHIKey	LHQDSEISPPGRMR-LJGZSNSNSA-N
Standard InCHI	InChI=1S/C38H52O8/c1-20(2)22-13-16-38(33(43)44)18-17-35(5)23(28(22)38)10-12-27-36(35,6)15-14-26-34(3,4)30(29(32(42)45-8)37(26,27)7)46-31(41)21-9-11-24(39)25(40)19-21/h9,11,19,22-23,26-30,39-40H,1,10,12-18H2,2-8H3,(H,43,44)/t22-,23+,26-,27-,28+,29+,30-,35+,36+,37-,38-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@H]([C@H](C(=O)OC)[C@]43C)OC(=O)c3ccc(c(c3)O)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.37	Volume:	666.332 ? Van der Waals volume.
Dense:	0.955	LogP:	4.762 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.891 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.547 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	34.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.173	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.138	Fsp³:	0.711
MCE-18:	169.923 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.83	Fluc inhibitor:	0.044 ? 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:	0.186	Promiscuous compounds:	0.195

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.38	MDCK Permeability:	-4.954
Pgp-inhibitor:	0.003	Pgp-substrate:	0.0
PAMPA:	0.768 ? 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%):	0.401	30% Bioavailability (F30%):	0.692
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	1.0
Plasma Protein Binding (PPB):	97.802%	Volume Distribution (VD):	-0.225
Fu:	2.083% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.051
BSEP inhibitor:	0.388

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.011	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.955	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.003 ? 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):

6.358

Half-life (T1/2):

1.233

ADMET: Toxicity

hERG Blockers:	0.07	hERG Blockers (10um):	0.235
Human Hepatotoxicity (H-HT):	0.461	Drug-induced Liver Injury (DILI):	0.884
AMES Toxicity:	0.23	Rat Oral Acute Toxicity:	0.217
Maximum Recommended Daily Dose:	0.611	Skin Sensitization:	0.996
Carcinogencity:	0.871	Eye Corrosion:	0.017
Eye Irritation:	0.678	Respiratory Toxicity:	0.657
Drug-induced Neurotoxicity:	0.021	Ototoxicity:	0.676
Hematotoxicity:	0.117	Drug-induced Nephrotoxicity:	0.597
Genotoxicity:	0.94	RPMI-8226 Immunitoxicity:	0.008
A549 Cytotoxicity:	0.277	Hek293 Cytotoxicity:	0.168
BCF:	0.764 ? 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:	4.086 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.569 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.072 ? 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
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2800.0	nM	PMID[27617953]

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 NPC486695 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	5867
0.1-0.2	39669
0.2-0.3	4090
0.3-0.4	157
0.4-0.5	46
0.5-0.6	18
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8171	Intermediate Similarity	NPC486697
0.7229	Intermediate Similarity	NPC486708
0.686	Remote Similarity	NPC290349
0.6322	Remote Similarity	NPC486706
0.6322	Remote Similarity	NPC486705
0.6196	Remote Similarity	NPC8102
0.6196	Remote Similarity	NPC66894
0.6022	Remote Similarity	NPC97475
0.6022	Remote Similarity	NPC486696
0.6	Remote Similarity	NPC487491
0.5926	Remote Similarity	NPC486704
0.5889	Remote Similarity	NPC486699
0.5806	Remote Similarity	NPC248287
0.5806	Remote Similarity	NPC234548
0.5625	Remote Similarity	NPC486700
0.5625	Remote Similarity	NPC275312
0.5567	Remote Similarity	NPC101863
0.5556	Remote Similarity	NPC205392
0.5556	Remote Similarity	NPC105942
0.5385	Remote Similarity	NPC486709
0.5347	Remote Similarity	NPC487490
0.5258	Remote Similarity	NPC475138
0.5244	Remote Similarity	NPC24772
0.5229	Remote Similarity	NPC478984
0.5143	Remote Similarity	NPC487488
0.5143	Remote Similarity	NPC487489
0.5119	Remote Similarity	NPC4309
0.5098	Remote Similarity	NPC487492

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2433
0.1-0.2	6549
0.2-0.3	164
0.3-0.4	1
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